Aminopropenoates as fungicides

ABSTRACT

The present invention relates to aminopropenoate derivatives, the process of their preparation, intermediate compounds, their use as fungicide active agents, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants and in material protection, using these compounds or compositions.

This application claims priority to European Patent Application No. 09173304.8, filed Oct. 16, 2009, and the benefit of U.S. Provisional Application No. 61/253,091, filed Oct. 20, 2009, the disclosure of each of which is incorporated by reference herein in its entirety.

The present invention relates to aminopropenoate derivatives, the process of their preparation, intermediate compounds, their use as fungicide active agents, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants and in material protection, using these compounds or compositions.

Certain aminopropenoate derivatives are already known as synthesis intermediates (cf. Journal fuer Praktische Chemie (Leipzig), 1988, 330(3), 361-6; Khimiya Geterotsiklicheskikh Soedinenii, 1991, (12), 1636-9; Egyptian Journal of Chemistry, 1999, 42(2), 175-187; Sulfur Letters, 1992, 15(2), 91-101; and Zeitschrift fuer Chemie, 1982, 22(2), 56. Others were prepared during the development of new chemical methodologies towards acrylates derivatives: Yakugaku Zasshi, 1967, 87(7), 857-60; Yakugaku Zasshi, 1967, 87(9), 1044-51; Jpn. Tokkyo Koho, 1970, JP45031283; Jpn. Tokkyo Koho, 1970, JP45031284; Yakugaku Zasshi, 1972, 92(12), 1468-72; J. Heterocyclic Chem.; 2007, 44, 505-513. Certain substituted 3-amino-2-cyano-3-phenylacrylate derivatives are known to exhibit fungicidal activities [cf. CN13171483A, CN101381326A and Youji Huaxue, 2005, 25(10), 1254-1258]. Other substituted 3-alkylamino-2-cyano-3-(het)arylacrylate derivatives are known to have the potency to inhibit growth and survival of cancerous cell lines (cf. WO 2005/058829). The compounds disclosed in these documents do not prove to provide a comparable utility than the compounds according to the invention.

Since the ecological and economical demands made on modem active compounds, for example fungicides, are increasing constantly, for example with respect to activity spectrum, toxicity, selectivity, application rate, formation of residues and favorable manufacture, and there can furthermore be problems, for example, with resistance, there is a constant need to develop novel fungicides which, at least in some areas, have advantages over those of the prior art. Surprisingly, it has now been found that aminopropenoates of the formula (I) (see below) are suitable as fungicides and, at least in some aspects, have improved properties compared to known fungicidally active compounds.

It has now been found that aminopropenoate derivatives of the general formula (I):

in which

-   R represents one of the following groups R^(A), R^(B) or R^(C)

-   n represents 0, 1, 2, 3 or 4, -   m represents 1, 2, 3 or 4, -   t represents 0 or 1, -   Y¹ represents S, O or NR⁵, -   Y² represents O, S or NR⁶, -   Y³ represents S, O or NR^(B), -   Y⁴ represents a bond or O, S or NR⁹, -   Y⁵ represents SO or SO₂, -   in case that Y² represents NR⁶, then R⁶ and R¹ together with the     nitrogen atom to which they are linked may form a 5- to 7-membered,     saturated or unsaturated, carbo- or heterocycle comprising up to 3     heteroatoms, which cycle may also include one of the groups C(═O)     and C(═S), -   in case that Y⁴ represents NR⁹, then R⁹ and R⁷ together with the     nitrogen atom to which they are linked may form a 5- to 7-membered,     saturated or unsaturated, carbo- or heterocycle comprising up to 3     heteroatoms, which cycle may also include one of the groups C(═O)     and C(═S), -   R¹ represents a hydrogen, C₁-C₈-alkyl, C₃-C₈-cycloalkyl,     C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be     the same or different, C₂-C₈-alkenyl, C₂-C₈-alkynyl,     C₃-C₈-cycloalkyl-C₁-C₈-alkyl, C₂-C₈-alkenyl-C₁-C₈-alkyl,     C₂-C₈-alkynyl-C₁-C₈-alkyl, C₁-C₈-halogeno-C₃-C₈-cycloalkyl     comprising up to 9 halogen atoms which can be the same or different,     C₃-C₈-cycloalkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl,     C₃-C₈-cycloalkoxy-C₁-C₈-alkyl, C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl     comprising up to 9 halogen atoms which can be the same or different,     C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl,     C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl comprising up to 9 halogen     atoms which can be the same or different,     C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl,     C₁-C₈-trialkylsilyl-C₁-C₈-alkyl, a benzotriazolyl, an     aryl-C₃-C₈-cycloalkyl which can be substituted by up to 5 groups Q;     and, provided that Y² does not represent NH, R¹ can also represent     an aryl which can be substituted by up to 5 groups Q, an     aryl-C₁-C₈-alkyl which can be substituted by up to 5 groups Q; -   Het represents one of the heterocycles Het 1 to Het 61:

-   R² and R³, which can be the same or different, independently of one     another represent hydrogen, halogen, CN, NH₂, NO₂, C₁-C₈-alkyl,     C₁-C₈-hydroxyalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halogenocycloalkyl     comprising up to 9 halogen atoms which can be the same or different,     C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be     the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl, C₂-C₈-alkenyl,     C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms which can be     the same or different, C₂-C₈-alkynyl, C₂-C₈-alkenyl-C₁-C₈-alkyl,     C₂-C₈-alkynyl-C₁-C₈-alkyl, C₃-C₈-halogenocycloalkyl comprising up to     9 halogen atoms which can be the same or different,     C₃-C₈-cycloalkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl,     C₁-C₈-alkoxy-C₂-C₈-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkynyl,     C₃-C₈-cycloalkoxy-C₁-C₈-alkyl, C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl     comprising up to 9 halogen atoms which can be the same or different,     C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl, C₁-C₈-alkylsulfinyl-C₁-C₈-alkyl,     C₁-C₈-alkylsulfonyl-C₁-C₈-alkyl, amino-C₁-C₈-alkyl,     C₁-C₈-alkylamino-C₁-C₈-alkyl, di-(C₁-C₈-alkyl)amino-C₁-C₈-alkyl,     C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl comprising up to 9 halogen     atoms which can be the same or different,     C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl,     C₁-C₈-trialkylsilyl, phenyl which can be substituted by up to 5     groups Q, phenyl-C₂-C₄-alkynyl, which can be substituted in the     phenyl moiety by up to 5 groups Q, -   R² and R³ also together with the carbon atom to which they are     linked can form a C₃-C₇-cycloalkyl, which may be substituted by 1 to     4 identical or different substituents selected from by halogen, OH,     C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio or     phenyl, or can form a C₅-C₁₀-bicycloalkyl, a     2,3-dihydro-1H-indene-1-yl or a decahydronaphthalenyl, -   R⁴ represents an aryl or a heterocycle E 1 to E 144:

-   R⁴ also represents hydrogen or halogen when n represents 1, 2, 3 or     4, -   R⁵ represents hydrogen, OH, C₁-C₈-alkyl, C₃-C₈-cycloalkyl,     C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be     the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl,     C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl,     halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms which can     be the same or different, C₃-C₈-cycloalkenyl,     C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl,     C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms     which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl,     C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl     comprising up to 9 halogen atoms which can be the same or different,     C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl,     an aryl which can be substituted by up to 5 groups Q, an     aryl-C₁-C₈-alkyl which can be substituted by up to 5 groups Q, an     aryl-C₃-C₈-cycloalkyl which can be substituted by up to 5 groups Q; -   R⁶ represents hydrogen, OH, C₁-C₈-alkyl, C₃-C₈-cycloalkyl,     C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be     the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl,     C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl,     halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms which can     be the same or different, C₃-C₈-cycloalkenyl,     C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl,     C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms     which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl,     C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl     comprising up to 9 halogen atoms which can be the same or different,     C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl,     C₁-C₈-alkoxy, C₃-C₈-cycloalkoxy, C₁-C₈-halogenoalkoxy comprising up     to 9 halogen atoms which can be the same or different,     C₃-C₈-cycloalkyl-C₁-C₈-alkoxy, C₂-C₈-alkenyl-C₁-C₈-alkoxy,     C₂-C₈-alkynyl-C₁-C₈-alkoxy, C₁-C₈-halogen-C₃-C₈-cycloalkoxy     comprising up to 9 halogen atoms which can be the same or different,     C₃-C₈-cycloalkenyloxy, C₁-C₈-alkoxy-C₁-C₈-alkoxy,     C₃-C₈-cycloalkoxy-C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy-C₁-C₈-alkoxy     comprising up to 9 halogen atoms which can be the same or different,     C₁-C₈-alkylsulfanyl-C₁-C₈-alkoxy, C₁-C₈-alkylamino-C₁-C₈-alkoxy,     C₁-C₈-halogenoalkylamino-C₁-C₈-alkoxy comprising up to 9 halogen     atoms which can be the same or different,     C₃-C₈-cycloalkylamino-C₁-C₈-alkoxy,     C₁-C₈-trialkylsilyl-C₁-C₈-alkoxy, aryloxy which can be substituted     by up to 5 groups Q, benzyloxy which can be substituted by up to 5     groups Q; C₁-C₈-alkylamino, (C₁-C₈-alkyl)carbonylamino,     C₃-C₈-cycloalkylamino, C₁-C₈-halogenoalkylamino comprising up to 9     halogen atoms which can be the same or different,     C₃-C₈-cycloalkyl-C₁-C₈-alkylamino, C₂-C₈-alkenyl-C₁-C₈-alkylamino,     C₂-C₈-alkynyl-C₁-C₈-alkylamino, halogeno-C₃-C₈-cycloalkylamino     comprising up to 9 halogen atoms which can be the same or different,     arylamino which can be substituted by up to 5 groups Q, benzylamino     which can be substituted by up to 5 groups Q, an     aryl-C₃-C₈-cycloalkyl which can be substituted by up to 5 groups Q; -   R⁷ represents hydrogen, C₁-C₈-alkyl, C₃-C₈-cycloalkyl,     C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be     the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl, C₂-C₈-alkenyl,     C₂-C₈-alkynyl, C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl,     halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms which can     be the same or different, C₃-C₈-cycloalkenyl,     C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl,     C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms     which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl,     C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl     comprising up to 9 halogen atoms which can be the same or different,     C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl,     phenyl or naphthyl, each of which can be substituted by up to 5     groups Q, benzyl which can be substituted by up to 5 groups Q,     phenyl-C₁-C₂-alkylimino, -   R⁷ also represents CN, if R is R^(B), t is 0 and Y⁴ is a bond, -   R⁸ represents hydrogen, OH, C₁-C₈-alkyl, C₃-C₈-cycloalkyl,     C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be     the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl,     C₂-C₃-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl,     C₁-C₈-halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms     which can be the same or different, C₃-C₈-cycloalkenyl,     C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl,     C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms     which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl,     C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl     comprising up to 9 halogen atoms which can be the same or different,     C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl,     phenyl which can be substituted by up to 5 groups Q, benzyl which     can be substituted by up to 5 groups Q; C₁-C₈-alkoxy,     C₃-C₈-cycloalkoxy, C₁-C₈-halogenoalkoxy comprising up to 9 halogen     atoms which can be the same or different,     C₃-C₈-cycloalkyl-C₁-C₈-alkoxy, C₂-C₈-alkenyl-C₁-C₈-alkoxy,     C₁-C₈-alkynyl-C₁-C₈-alkoxy, C₁-C₈-halogeno-C₃-C₈-cycloalkoxy     comprising up to 9 halogen atoms which can be the same or different,     C₃-C₈-cycloalkenyloxy, C₁-C₈-alkoxy-C₁-C₈-alkoxy,     C₃-C₈-cycloalkoxy-C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy-C₁-C₈-alkoxy     comprising up to 9 halogen atoms which can be the same or different,     C₁-C₈-alkylsulfanyl-C₁-C₈-alkoxy, C₁-C₈-alkylamino-C₁-C₈-alkoxy,     C₁-C₈-halogenoalkylamino-C₁-C₈-alkoxy comprising up to 9 halogen     atoms which can be the same or different,     C₃-C₈-cycloalkylamino-C₁-C₈-alkoxy,     C₁-C₈-trialkylsilyl-C₁-C₈-alkoxy, aryloxy which can be substituted     by up to 5 groups Q, benzyloxy which can be substituted by up to 5     groups Q, -   R⁹ represents hydrogen, OH, C₁-C₈-alkyl, C₃-C₈-cycloalkyl,     C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be     the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl,     C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl,     C₃-C₈-halogenocycloalkyl comprising up to 9 halogen atoms which can     be the same or different, C₃-C₈-cycloalkenyl,     C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl,     C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms     which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl,     C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl     comprising up to 9 halogen atoms which can be the same or different,     C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl,     phenyl which can be substituted by up to 5 groups Q, benzyl which     can be substituted by up to 5 groups Q; C₁-C₈-alkoxy,     C₃-C₈-cycloalkoxy, C₁-C₈-halogenoalkoxy comprising up to 9 halogen     atoms which can be the same or different,     C₃-C₈-cycloalkyl-C₁-C₈-alkoxy, C₂-C₈-alkenyl-C₁-C₈-alkoxy,     C₂-C₈-alkynyl-C₁-C₈-alkoxy, halogeno-C₃-C₈-cycloalkoxy comprising up     to 9 halogen atoms which can be the same or different,     C₃-C₈-cycloalkenyloxy, C₁-C₈-alkoxy-C₁-C₈-alkoxy,     C₃-C₈-cycloalkoxy-C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy-C₁-C₈-alkoxy     comprising up to 9 halogen atoms which can be the same or different,     C₁-C₈-alkylsulfanyl-C₁-C₈-alkoxy, C₁-C₈-alkylamino-C₁-C₈-alkoxy,     C₁-C₈-halogenoalkylamino-C₁-C₈-alkoxy comprising up to 9 halogen     atoms which can be the same or different,     C₃-C₈-cycloalkylamino-C₁-C₈-alkoxy,     C₁-C₈-trialkylsilyl-C₁-C₈-alkoxy, phenyloxy which can be substituted     by up to 5 groups Q, benzyloxy which can be substituted by up to 5     groups Q, -   Q which can be the same or different, independently represents     halogen, CN, NO₂, C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylsulfanyl,     C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be     the same or, C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms     which can be the same or different, tri(C₁-C₈)alkylsilyl or     tri(C₁-C₈)alkylsilyl-C₁-C₈-alkyl, or two vicinal substituents Q may     be —OCH₂O—, —OCF₂O—, —O(CH₂)₂O—, —O(CF₂)₂O— or —N—CH—S—, -   Z¹, Z², Z³, Z⁴ Z⁵, Z⁶, Z⁷, Z⁸, Z⁹, Z¹⁰ and Z¹¹ which can be the same     or different, independently of one another represent hydrogen,     halogen, NO₂, CN, OH, SH, NH₂, SF₅, C₁-C₈-alkyl, C₁-C₈-halogenoalkyl     comprising up to 9 halogen atoms which can be the same or different     and optionally in addition one hydroxy group, C₁-C₈-alkylamino,     di-C₁-C₈-alkylamino, C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy comprising     up to 9 halogen atoms which can be the same or different,     C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylsulfanyl,     C₁-C₈-halogenoalkylsulfanyl comprising up to 9 halogen atoms which     can be the same or different, C₂-C₈-alkenyl, C₂-C₈-halogenoalkenyl     comprising up to 9 halogen atoms which can be the same or different,     C₂-C₈-alkynyl, C₂-C₈-halogenoalkynyl comprising up to 9 halogen     atoms which can be the same or different, C₂-C₈-alkenyloxy,     C₂-C₈-halogenoalkenyloxy comprising up to 9 halogen atoms which can     be the same or different, C₂-C₈-alkynyloxy, C₂-C₈-halogenoalkynyloxy     comprising up to 9 halogen atoms which can be the same or different,     C₂-C₈-alkenylsulfanyl, C₂-C₈-alkynylsulfanyl, C₃-C₇-cycloalkyl,     C₃-C₇-cycloalkyl-C₁-C₈-alkyl, C₃-C₇-halogenocycloalkyl comprising up     to 9 halogen atoms which can be the same or different, formyl,     formyloxy, formylamino, carbamoyl, N-hydroxycarbamoyl,     (hydroxyimino)-C₁-C₈-alkyl, C₁-C₈-alkylcarbonyl,     C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms which     can be the same or different, (C₃-C₇-cycloalkyl)carbonyl,     C₁-C₈-alkylcarbamoyl, di-C₁-C₈-alkylcarbamoyl,     N—C₁-C₈-alkoxycarbamoyl, C₁-C₈-alkoxycarbamoyl,     N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, C₁-C₈-alkoxycarbonyl,     C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms which     can be the same or different, C₁-C₈-alkylaminocarbonyl,     di-(C₁-C₈-alkyl)aminocarbonyl, C₁-C₈-alkylcarbonyloxy,     C₁-C₈-halogenoalkylcarbonyloxy comprising up to 9 halogen atoms     which can be the same or different, C₁-C₃-alkylcarbonylamino,     C₁-C₈-halogenoalkylcarbonylamino comprising up to 9 halogen atoms     which can be the same or different, C₁-C₈-alkylaminocarbonyloxy,     di-(C₁-C₈-alkyl)-aminocarbonyloxy, C₁-C₈-alkoxycarbonyloxy,     C₁-C₈-alkylsulphinyl, C₁-C₈-halogenoalkylsulphinyl comprising up to     9 halogen atoms which can be the same or different,     C₁-C₈-alkylsulphonyl, C₁-C₈-halogenoalkylsulphonyl comprising up to     9 halogen atoms which can be the same or different,     C₁-C₈-alkoxyimino, (C₁-C₈-alkylimino)-C₁-C₈-alkyl,     (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl,     (C₁-C₈-alkenyloxyimino)-C₁-C₈-alkyl,     (C₂-C₈-alkynyloxyimino)-C₁-C₈-alkyl, a (benzyloxyimino)-C₁-C₈-alkyl,     tri-(C₁-C₈-alkyl)silyl, tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, benzyloxy     which can be substituted by up to 5 groups Q, benzylsulfanyl which     can be substituted by up to 5 groups Q, benzylamino which can be     substituted by up to 5 groups Q, phenyl which can be substituted by     up to 5 groups Q, naphthyl which can be substituted by up to 6     groups Q, phenoxy which can be substituted by up to 5 groups Q,     phenylamino which can be substituted by up to 5 groups Q,     phenylsulfanyl which can be substituted by up to 5 groups Q,     phenylmethylene which can be substituted by up to 5 groups Q. -   or two vicinal substituents Z together with the consecutive carbon     atoms to which they are linked form a 5- or 6-membered, saturated or     unsaturated, carbo- or heterocycle comprising up to 3 heteroatoms,     which can be substituted by up to four groups Q which can be the     same or different and the other substituents Z are as     herein-described, -   or two geminal substitutents Z together with the carbon atom to     which they are linked could also be fused to represent C(═O); C(═S),     C₃-C₉-cycloalkyl;

G¹ and G² which can be the same or different, independently of one another represent hydrogen, CN, OH, NH₂, C₁-C₈-alkyl, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylamino, di-C₁-C₈-alkylamino, C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₂-C₈-alkenyl, C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different, C₂-C₈-alkynyl, C₂-C₈-halogenoalkynyl comprising up to 9 halogen atoms which can be the same or different C₂-C₈-alkenyloxy, C₂-C₈-halogenoalkenyloxy comprising up to 9 halogen atoms which can be the same or different, C₂-C₈-alkynyloxy, C₂-C₈-halogenoalkynyloxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₈-alkyl, C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, formyl, carbamoyl, (hydroxyimino)-C₁-C₈-alkyl, C₁-C₈-alkylcarbonyl, C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylcarbamoyl, C₁-C₈-alkoxycarbonyl, C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylaminocarbonyl, di-C₁-C₈-alkylaminocarbonyl, C₁-C₈-alkylsulphonyl, C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms which can be the same or different, (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl, (C₁-C₈-alkenyloxyimino)-C₁-C₈-alkyl, (C₂-C₈-alkynyloxyimino)-C₁-C₈-alkyl, a (benzyloxyimino)-C₁-C₈-alkyl, tri(C₁-C₈-alkyl)silyl, tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, benzyloxy which can be substituted by up to 5 groups Q, benzylamino which can be substituted by up to 5 groups Q, phenyl which can be substituted by up to 5 groups Q; naphthyl which can be substituted by up to 6 groups Q, phenoxy which can be substituted by up to 5 groups Q, phenylamino which can be substituted by up to 5 groups Q, phenylmethylene which can be substituted by up to 5 groups Q,

provided that

-   -   when n represents 1 then R², R³ and R⁴ do not represent         simultaneously a hydrogen atom,     -   when Het represents Het 42, Y¹ and Y² represent O, R¹ represents         ethyl, then Z³ does not represent hydrogen or NO₂,     -   when Het represents Het 8 and n represents O, then R⁴ does not         represent an unsubstituted phenyl group,     -   when Het represents an indole ring then R¹³ does not represent         —CH₂—CH₂—OH, —CH₂—OCOC₂H₅, —CH₂—CH₂—N(C₂H₅)₂,     -   when Het represents a 4,5,6,7-tetrahydro-1H-indole then R^(A)         does not represent n-butyl,         as well as salts, N-oxides, metallic complexes, metalloidic         complexes and optically active or geometric isomers thereof.

Depending on the nature of the substituents defined above, the compounds of the formula (I) have acidic or basic properties and can form salts, if appropriate also inner salts or adducts, with inorganic or organic acids or with inorganic or organic bases or with metal ions. Suitable metal ions are in particular the ions of the elements of the second main group, in particular calcium and magnesium, of the third and fourth main group, in particular aluminum, tin and lead, and also of the first to eighth transition group, in particular chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Particular preference is given to the metal ions of the elements of the fourth period. Here, the metals can be present in the various valencies they can assume.

If the compounds of the formula (I) carry hydroxyl groups, carboxyl groups or other groups which induce acidic properties, these compounds can be converted with bases into salts. Suitable bases are, for example, the hydroxides, carbonates and bicarbonates of the alkali metals and the alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, furthermore ammonia, primary, secondary and tertiary amines having C₁-C₄-alkyl radicals, mono-, di- and trialkanolamines of C₁-C₄-alkanols, choline and also chlorocholine.

If the compounds of the formula (I) carry amino groups, alkylamino groups or other groups which induce basic properties, these compounds can be converted with acids into salts. Examples of inorganic acids are hydrohalic acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid, sulphuric acid, phosphoric acid and nitric acid, and acidic salts, such as NaHSO₄ and KHSO₄. Suitable organic acids are, for example, formic acid, carbonic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulphonic acids (sulphonic acids having straight-chain or branched alkyl radicals of 1 to 20 carbon atoms), arylsulphonic acids or -disulphonic acids (aromatic radicals, such as phenyl and naphthyl which carry one or two sulphonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals of 1 to 20 carbon atoms), arylphosphonic acids or -diphosphonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two phosphonic acid radicals, where the alkyl radicals and aryl radicals may carry further substituents, for example p-toluenesulphonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.

The salts which can be obtained in this manner also have fungicidal properties.

Compounds of the formula (I) according to the invention can, if appropriate, be present as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z, threo and erythro, and also optical isomers, atropoisomers, and, if appropriate, also of tautomers. What is claimed are both the E and the Z isomers and the threo and erythro and also the optical isomers, any mixtures of these isomers, and also the possible tautomeric forms.

In particular the aminopropenoate derivatives of the formula (I) may exist in Z-form or in E-form, where the correct assignment of Z and E according to the IUPAC nomenclature depends on the definitions of the different substituents. For easy reference in this patent application the assignment is made as shown. In all formulas below and above the E-form is used. Nevertheless the Z-form is also part of this invention.

According to the invention, the following generic terms are generally used with the following meanings:

-   -   Halogen means fluorine, chlorine, bromine or iodine.     -   Heteroatom can be nitrogen, oxygen or sulphur.     -   Aryl means phenyl or naphthyl, optionally substituted by one to         five groups selected from the group consisting of halogen,         C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,         C₂-C₈-alkynyl, C₂-C₆-haloalkynyl, C₁-C₆-alkoxy,         C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy,         C₁-C₆-haloalkoxy and C₁-C₄-haloalkoxy-C₁-C₄-alkyl.     -   Any alkyl, alkenyl or alkynyl group can be linear or branched.

The formula (I) provides a general definition of the aminopropenoate derivatives which can be used according to the invention. Preferred radical definitions of the formulae given above and below are indicated below. These definitions apply both to the end products of the formula (I) and likewise to all intermediates. These definitions apply both to the end products of the formula (I) and likewise to all intermediates.

Preferred compounds of formula (I) according to the invention are those wherein R represents R^(A). Other preferred compounds of formula (I) according to the invention are those wherein R represents R^(B).

Preferred compounds of formula (I) according to the invention are those wherein n represents 0, 1, 2 or 3. More preferred compounds of formula (I) according to the invention are those wherein n represents 0, 1 or 2.

Preferred compounds of formula (I) according to the invention are those wherein m represents 1, 2 or 3. More preferred compounds of formula (I) according to the invention are those wherein m represents 1 or 2.

Preferred compounds of formula (I) according to the invention are those wherein Y¹ represents S, O. More preferred compounds of formula (I) according to the invention are those wherein Y¹ represents O.

Preferred compounds of formula (I) according to the invention are those wherein Y² represents O or NR⁶. More preferred compounds of formula (I) according to the invention are those wherein Y² represents O or NR⁶ wherein R⁶ represents hydrogen, C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl, C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl, C₁-C₈-halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl, C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl, C₁-C₈-alkoxy.

Even more preferred compounds of formula (I) according to the invention are those wherein Y² represents O or NR⁶ wherein R⁶ represents hydrogen, methyl, methoxy or ethoxy.

Preferred compounds of formula (I) according to the invention are those wherein Y³ represents O or NR⁸. More preferred compounds of formula (I) according to the invention are those wherein Y³ represents O or NR⁸ wherein R⁸ represents hydrogen, C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl, C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl, C₁-C₈-halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl, C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy, C₁-C₆-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₆-alkoxy, C₂-C₆-alkenyl-C₁-C₆-alkoxy, C₂-C₆-alkynyl-C₁-C₆-alkoxy, C₁-C₆-halogeno-C₃-C₆-cycloalkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkenyloxy, C₁-C₆-alkoxy-C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy-C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy-C₁-C₆-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulfanyl-C₁-C₆-alkoxy, C₁-C₆-alkylamino-C₁-C₆-alkoxy, C₁-C₆-halogenoalkylamino-C₁-C₆-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkylamino-C₁-C₆-alkoxy, C₁-C₆-trialkylsilyl-C₁-C₆-alkoxy, aryloxy which can be substituted by up to 5 groups Q, benzyloxy which can be substituted by up to 5 groups Q.

Even more preferred compounds of formula (I) according to the invention are those wherein Y³ represents O or NR⁸ wherein R⁸ represents hydrogen or methyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-, s- or t-butoxy, trifluoromethoxy, difluoromethoxy.

Preferred compounds of formula (I) according to the invention are those wherein Y⁴ represents a bond, O or NR⁹.

More preferred compounds of formula (I) according to the invention are those wherein Y⁴ represents a bond, O or NR⁹ wherein R⁹ represents hydrogen or C₁-C₆-alkyl.

Even more preferred compounds of formula (I) according to the invention are those wherein Y⁴ represents a bond, O or NR⁹ wherein R⁹ represents hydrogen, methyl or ethyl.

Preferred compounds of formula (I) according to the invention are those wherein R¹ represents hydrogen, C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₈-cycloalkyl-C₁-C₈-alkyl, C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl, C₁-C₈-halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl, C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogeno alkylamino-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl.

More preferred compounds of formula (I) according to the invention are those wherein R¹ represents hydrogen, C₁-C₈-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl.

Even more preferred compounds of formula (I) according to the invention are those wherein R¹ represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-, s-, t-butyl, cyclopropyl, cyclobutyl, trifluoropropyl, trifluoroethyl, allyl, propargyl, methoxymethyl, ethoxyethyl, ethoxymethyl, methoxyethyl.

Preferred compounds of formula (I) according to the invention are those wherein Het is selected in the list of Het 1 to Het 61, wherein Z¹, Z², Z³, Z⁴ and Z⁵ which can be the same or different, independently of one another represent hydrogen, halogen, NO₂, CN, OH, SH, NH₂, C₁-C₆-alkyl, C₁-C₆-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulfanyl, C₁-C₆-halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different, C₂-C₆-alkenyl, C₂-C₆-halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different, C₂-C₆-alkynyl, C₂-C₆-halogenoalkynyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₈-alkyl, C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, formyl, formyloxy, formylamino, carbamoyl, C₁-C₆-alkylcarbonyl, C₁-C₆-halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylcarbamoyl, di-C₁-C₆-alkylcarbamoyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylcarbonyloxy, C₁-C₆-halogenoalkylcarbonyloxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylcarbonylamino, C₁-C₆-halogenoalkylcarbonylamino comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulphinyl, C₁-C₆-halogenoalkylsulphinyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulphonyl, C₁-C₆-halogenoalkylsulphonyl comprising up to 9 halogen atoms which can be the same or different, tri(C₁-C₆-alkyl)silyl, tri(C₁-C₆-alkyl)silyl-C₁-C₆-alkyl, benzyloxy which can be substituted by up to 5 groups Q, benzylamino which can be substituted by up to 5 groups Q, phenyl which can be substituted by up to 5 groups Q; naphthyl which can be substituted by up to 6 groups Q, phenoxy which can be substituted by up to 5 groups Q, phenylamino which can be substituted by up to 5 groups Q, phenylsulfanyl which can be substituted by up to 5 groups Q, or two vicinal substituents Z together with the consecutive carbon atoms to which they are linked form a 5- or 6-membered, saturated, carbo- or hetero-cycle comprising up to 3 heteroatoms, which can be substituted by up to four groups Q which can be the same or different and the other substituents Z are as herein-described and Q, which can be the same or different, represents a halogen atom, cyano group, nitro group, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, tri(C₁-C₆)alkylsilyl or tri(C₁-C₆)alkylsilyl-C₁-C₆-alkyl. And G¹ and G² which can be the same or different, represent a hydrogen atom, cyano group, hydroxyl, amino, C₁-C₆-alkyl, C₁-C₆-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₆-alkyl, C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, formyl, C₁-C₆-alkylcarbonyl, C₁-C₆-halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylcarbamoyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylsulphonyl, C₁-C₆-halogenoalkylsulphonyl comprising up to 9 halogen atoms which can be the same or different, tri(C₁-C₆-alkyl)silyl, tri(C₁-C₆-alkyl)silyl-C₁-C₆-alkyl, phenyl which can be substituted by up to 5 groups Q; phenylmethylene which can be substituted by up to 5 groups Q.

More preferred compounds of formula (I) according to the invention are those wherein Het is selected in the list of Het 1 to Het 12, Het 15 to Het 22, Het 25, Het 27, Het 28, Het 30, Het 33 to Het 43, Het 46 to Het 53, Het 55 to Het 59 and Het 61, wherein Z¹, Z², Z³, Z⁴ and Z⁵ which can be the same or different, independently of one another represent hydrogen, halogen, NO₂, CN, OH, SH, NH₂, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₇-cycloalkyl, C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-alkylcarbonyl, C₁-C₄-halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-alkoxycarbonyl, C₁-C₄-halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-alkylcarbonyloxy, C₁-C₄-halogenoalkylcarbonyloxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-alkylcarbonylamino, C₁-C₄-halogenoalkylcarbonylamino comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-alkylsulfanyl, C₁-C₄-halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-alkylsulphonyl, C₁-C₄-halogenoalkylsulphonyl comprising up to 9 halogen atoms which can be the same or different, tri(C₁-C₄-alkyl)silyl, phenyl which can be substituted by up to 5 groups Q; naphthyl which can be substituted by up to 6 groups Q, or two vicinal substituents Z together with the consecutive carbon atoms to which they are linked form 6-membered, unsaturated carbocycle which can be substituted by up to four groups Q which can be the same or different and the other substituents Z are as herein-described and Q, which can be the same or different, represents a halogen atom, cyano group, nitro group, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, tri(C₁-C₄)alkylsilyl And G′ and G² which can be the same or different, represent a hydrogen atom, C₁-C₄ alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, formyl, C₁-C₄-alkylcarbonyl, C₁-C₄-halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different.

Even more preferred compounds of formula (I) according to the invention are those wherein Het is selected in the list of Het 1 to Het 3, Het 8 to Het 11, Het 25, Het 30, Het 36, Het 37, Het 39 to Het 43, Het 46 to Het 50, Het 52, Het 53 and Het 61, wherein Z¹, Z², Z³, Z⁴ and Z⁵ which can be the same or different, independently of one another represent hydrogen, halogen, NO₂, CN, OH, SH, NH₂, methyl, ethyl, n-propyl, isopropyl, n-, s- or t-butyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, methylamino, ethylamino, dimethylamino, diethylamino, methoxy, ethoxy, trifluoromethoxy, vinyl, allyl, ethinyl, propargyl, cyclopropyl, cyclohexyl, acetyl, C₁-C₃-halogenoalkylcarbonyl comprising up to 5 halogen atoms which can be the same or different, carboxyl, methoxycarbonyl, ethoxycarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkylcarbonylamino, C₁-C₄-halogenoalkylcarbonylamino comprising up to 5 halogen atoms which can be the same or different, methylthio, ethylthio, trimethylsilyl, phenyl which can be substituted by up to 3 groups Q; naphthyl which can be substituted by up to 6 groups Q.

Q, which can be the same or different, independently preferably represents halogen, CN, NO₂, C₁-C₈-alkyl, C₁-C₆-alkoxy, C₁-C₆-halogenoalkyl comprising up to 5 halogen atoms which can be the same or different, C₁-C₆-halogenoalkoxy comprising up to 5 halogen atoms which can be the same or different, tri(C₁-C₈-alkylsilyl.

G¹ and G² which can be the same or different, independently of one another represent hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-halogenoalkyl comprising up to 5 halogen atoms which can be the same or different, C₃-C₆-halogenocycloalkyl comprising up to 5 halogen atoms which can be the same or different, C₁-C₆-alkylcarbonyl, C₁-C₆-halogenoalkylcarbonyl comprising up to 5 halogen atoms which can be the same or different.

More preferred G¹ and G² which can be the same or different, independently of one another represent hydrogen, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkylcarbonyl.

Even more preferred G¹ and G² which can be the same or different, independently of one another represent hydrogen or methyl.

Preferred compounds of formula (I) according to the invention are those wherein R² and R³, which can be the same or different, independently of one another represent hydrogen, halogen, CN, NH₂, C₁-C₆-alkyl, C₁-C₆-hydroxyalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₂-C₆-alkenyl-C₁-C₆-alkyl, C₂-C₆-alkynyl-C₁-C₆-alkyl, C₃-C₆-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₆-cycloalkoxy-C₁-C₆-alkyl, C₁-C₆-halogenoalkoxy-C₁-C₆-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulfanyl-C₁-C₆-alkyl, C₁-C₆-alkylamino-C₁-C₆-alkyl, C₁-C₆-halogenoalkylamino-C₁-C₆-alkyl comprising up to 9 halogen atoms which can be the same or different, R₂ and R₃ together with the carbon atom to which they are linked can form a C₃-C₇ cycloalkyl.

More preferred compounds of formula (I) according to the invention are those wherein R² and R³, which can be the same or different, independently of one another represent hydrogen, halogen, CN, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-halogenoalkyl comprising up to 5 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₂-C₄-alkenyl-C₁-C₄-alkyl, C₂-C₄-alkynyl-C₁-C₄-alkyl, C₃-C₄-halogenocycloalkyl comprising up to 5 halogen atoms which can be the same or different, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, C₁-C₄-halogenoalkoxy-C₁-C₄-alkyl comprising up to 5 halogen atoms which can be the same or different, R₂ and R₃ together with the carbon atom to which they are linked can form a C₃-C₆-cycloalkyl which may be substituted by 1 to 4 identical or different substituents selected from by fluorine, chlorine, bromine, OH, methyl, ethyl, n-propyl, isopropyl, n-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio, or phenyl.

Even more preferred compounds of formula (I) according to the invention are those wherein R² and R³, which can be the same or different, independently of one another represent hydrogen, halogen, CN, methyl, ethyl, n-propyl, isopropyl, n-, s- or t-butyl, cyclopropyl, 1-chlorocyclopropyl, trifluoromethyl, trifluoroethyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₂-C₆-alkenyl-C₁-C₆-alkyl, C₂-C₆-alkynyl-C₁-C₈-alkyl, C₃-C₆-halogenocycloalkyl comprising up to 5 halogen atoms which can be the same or different, R₂ and R₃ together with the carbon atom to which they are linked can form a C₃-C₆-cycloalkyl which may be substituted by 1 to 4 identical or different substituents selected from by fluorine, chlorine, bromine, OH, methyl, ethyl, n-propyl, isopropyl, n-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio, or phenyl.

Preferred compounds of formula (I) according to the invention are those wherein R⁴ is selected from the group consisting of E 1 to E 144, wherein Z¹, Z², Z³, Z⁴, Z⁵, Z⁶, Z⁷, Z⁸, Z⁹, Z¹⁰ and Z¹¹ which can be the same or different, independently of one another represent hydrogen, halogen, NO₂, CN, OH, SH, NH₂, C₁-C₆-alkyl, C₁-C₆-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different and optionally in addition one hydroxy group, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulfanyl, C₁-C₆-halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different, C₂-C₆-alkenyl, C₂-C₆-halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different, C₂-C₆-alkynyl, C₂-C₆-halogenoalkynyl comprising up to 9 halogen atoms which can be the same or different, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₂-C₆-alkenylsulfanyl, C₂-C₆-alkynylsulfanyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₆-alkyl, C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, formyl, formyloxy, formylamino, carbamoyl, C₁-C₆-alkylcarbonyl, (C₃-C₆-cycloalkyl)carbonyl, C₁-C₆-halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylcarbamoyl, di-C₁-C₆-alkylcarbamoyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylcarbonyloxy, C₁-C₆-halogenoalkylcarbonyloxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylcarbonylamino, C₁-C₆-halogenoalkylcarbonylamino comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulfanyl, C₁-C₆-halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulphinyl, C₁-C₆-halogenoalkylsulphinyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulphonyl, C₁-C₆-halogenoalkylsulphonyl comprising up to 9 halogen atoms which can be the same or different, tri(C₁-C₆-alkyl)silyl, tri(C₁-C₆-alkyl)silyl-C₁-C₆-alkyl, benzyloxy which can be substituted by up to 5 groups Q, benzylamino which can be substituted by up to 5 groups Q, phenyl which can be substituted by up to 5 groups Q; naphthyl which can be substituted by up to 6 groups Q, phenoxy which can be substituted by up to 5 groups Q, phenylamino which can be substituted by up to 5 groups Q, phenylsulfanyl which can be substituted by up to 5 groups Q, or two vicinal substituents Z together with the consecutive carbon atoms to which they are linked form a 5- or 6-membered, saturated, carbo- or hetero-cycle comprising up to 3 heteroatoms, which can be substituted by up to four groups Q which can be the same or different and the other substituents Z are as herein-described and Q, which can be the same or different, represents a halogen atom, cyano group, nitro group, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, tri(C₁-C₆)alkylsilyl or tri(C₁-C₆)alkylsilyl-C₁-C₆-alkyl. And G¹ and G² which can be the same or different, represent a hydrogen atom, cyano group, hydroxyl, amino, C₁-C₆-alkyl, C₁-C₆-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₆-alkyl, C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, formyl, C₁-C₆-alkylcarbonyl, C₁-C₆-halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylcarbamoyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylsulphonyl, C₁-C₆-halogenoalkylsulphonyl comprising up to 9 halogen atoms which can be the same or different, tri(C₁-C₆-alkyl)silyl, tri(C₁-C₆-alkyl)silyl-C₁-C₆-alkyl, phenyl which can be substituted by up to 5 groups Q; phenylmethylene which can be substituted by up to 5 groups Q.

In the case Z¹, Z², Z³, Z⁴, Z⁵, Z⁶, Z⁷, Z⁸, Z⁹, Z¹⁰, Z¹¹ are geminals they could also be fused to represent (═O); (═S),

Two geminal substituents Z together with the carbon atom to which they are linked could preferably also be fused to represent C(═O) or C(═S).

More preferred compounds of formula (I) according to the invention are those wherein R⁴ is selected in the list of E 1 to E 86, E 89 to E 95, E 98 to E 112, E 129, E 130 and E 133 to E 141 wherein Z¹, Z², Z³, Z⁵, Z⁶, Z⁷, Z⁸, Z⁹, Z¹⁰ and Z¹¹ which can be the same or different, independently of one another represent hydrogen, halogen, NO₂, CN, OH, SH, NH₂, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different and optionally in addition one hydroxy group, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy, C₁-C₄-alkylsulfanyl, C₂-C₄-alkenylsulfanyl, C₂-C₄-alkynylsulfanyl, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, C₁-C₄-halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-halogenoalkylsulphenyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-halogenoalkylsulphonyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₇-cycloalkyl, C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-alkylcarbonyl, C₁-C₄-halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-alkoxycarbonyl, C₁-C₄-halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-alkylcarbonyloxy, C₁-C₄-halogenoalkylcarbonyloxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-alkylcarbonylamino, C₁-C₄-halogenoalkylcarbonylamino comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-alkylsulfanyl, C₁-C₄-halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-alkylsulphonyl, halogenoalkylsulphonyl comprising up to 9 halogen atoms which can be the same or different, tri(C₁-C₄-alkyl)silyl, phenyl which can be substituted by up to 5 groups Q; naphthyl which can be substituted by up to 6 groups Q, phenoxy or phenylthio, or two vicinal substituents Z together with the consecutive carbon atoms to which they are linked form 6-membered, unsaturated which can be substituted by up to four groups Q which can be the same or different and the other substituents Z are as herein-described and Q, which can be the same or different, represents a halogen atom, cyano group, nitro group, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, tri(C₁-C₄)alkylsilyl And G¹ and G² which can be the same or different, represent a hydrogen atom, C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, formyl, C₁-C₄-alkylcarbonyl, C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different.

Even more preferred compounds of formula (I) according to the invention are those wherein R⁴ is selected in the list of E 1 to E 48, E 52 to E 56, E 63, E 64, E 69 to E 77, E 98 to E 100, E 105, E 106, E 109 to E 112, E 129 and E 130, wherein Z¹, Z², Z³, Z⁴, Z⁵, Z⁶, Z⁷, Z⁸, Z⁹, Z¹⁰ an Z¹¹ which can be the same or different, independently of one another represent hydrogen, halogen, NO₂, CN, OH, SH, NH₂, methyl, ethyl, n-propyl, isopropyl, n-, s- or t-butyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, methylamino, ethylamino, dimethylamino, diethylamino, methoxy, ethoxy, trifluoromethoxy, vinyl, allyl, ethinyl, propargyl, cyclopropyl, cyclohexyl, acetyl, C₁-C₃-halogenoalkylcarbonyl comprising up to 5 halogen atoms which can be the same or different, carboxyl, methoxycarbonyl, ethoxycarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkylcarbonylamino, methylthio, ethylthio, trimethylsilyl, phenyl which can be substituted by up to 3 groups Q; naphthyl which can be substituted by up to 6 groups Q.

Two geminal substituents Z together with the carbon atom to which they are linked could preferably also be fused to represent C(═O).

G¹ and G² which can be the same or different, independently of one another represent hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-halogenocycloalkyl comprising up to 5 halogen atoms which can be the same or different, C₁-C₆-alkylcarbonyl, C₁-C₆-halogenoalkylcarbonyl comprising up to 5 halogen atoms which can be the same or different.

Preferred compounds of formula (I) according to the invention are those wherein at least one substituent Z of a group Het 1 to Het 61 is not hydrogen.

More preferred compounds of formula (I) according to the invention are those wherein the substituent Z¹ of a group Het 1 to Het 61 is not hydrogen.

Preferred compounds of formula (I) according to the invention are those wherein R⁵ represents hydrogen, OH, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₂-C₆-alkenyl-C₁-C₆-alkyl, C₂-C₆-alkynyl-C₁-C₆-alkyl, halogeno-C₃-C₆-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₆-cycloalkoxy-C₁-C₆-alkyl, C₁-C₆-halogenoalkoxy-C₁-C₆-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulfanyl-C₁-C₆-alkyl, C₁-C₆-alkylamino-C₁-C₆-alkyl, C₁-C₆-halogenoalkylamino-C₁-C₆-alkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkylamino-C₁-C₆-alkyl, C₁-C₆-trialkylsilyl-C₁-C₆-alkyl, an aryl which can be substituted by up to 5 groups Q, an aryl-C₁-C₆-alkyl which can be substituted by up to 5 groups Q, an aryl-C₃-C₆-cycloalkyl which can be substituted by up to 5 groups Q.

More preferred compounds of formula (I) according to the invention are those wherein R⁵ represents hydrogen, OH, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₂-halogenoalkyl comprising up to 5 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₂-alkyl, C₂-C₄-alkenyl-C₁-C₄-alkyl, C₂-C₄-alkynyl-C₁-C₄-alkyl, halogeno-C₃-C₆-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, cyclohexenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₆-cycloalkoxy-C₁-C₄-alkyl, C₁-C₄-halogenoalkoxy-C₁-C₄-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-alkylsulfanyl-C₁-C₄-alkyl, C₁-C₄-alkylamino-C₁-C₄-alkyl, C₁-C₄-halogenoalkylamino-C₁-C₄-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-trialkylsilyl-C₁-C₄-alkyl, phenyl or naphthyl, each of which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q.

Preferred compounds of formula (I) according to the invention are those wherein R⁶ represents hydrogen, OH, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₇-C₆-alkenyl-C₁-C₆-alkyl, C₂-C₆-alkynyl-C₁-C₆-alkyl, halogeno-C₃-C₆-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₆-cycloalkoxy-C₁-C₆-alkyl, C₁-C₆-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulfanyl-C₁-C₆-alkyl, C₁-C₆-alkylamino-C₁-C₆-alkyl, C₁-C₆-halogenoalkylamino-C₁-C₆-alkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkylamino-C₁-C₆-alkyl, C₁-C₆-trialkylsilyl-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy, C₁-C₆-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₆-alkoxy, C₂-C₆-alkenyl-C₁-C₆-alkoxy, C₂-C₆-alkynyl-C₁-C₆-alkoxy, C₁-C₆-halogeno-C₃-C₆-cycloalkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkenyloxy, C₁-C₆-alkoxy-C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy-C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy-C₁-C₆-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulfanyl-C₁-C₆-alkoxy, C₁-C₆-alkylamino-C₁-C₆-alkoxy, C₁-C₆-halogenoalkylamino-C₁-C₆-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkylamino-C₁-C₆-alkoxy, C₁-C₆-trialkylsilyl-C₁-C₆-alkoxy, aryloxy which can be substituted by up to 5 groups Q, benzyloxy which can be substituted by up to 5 groups Q; C₁-C₆-alkylamino, (C₁-C₄-alkyl)carbonylamino, C₃-C₆-cycloalkylamino, C₁-C₆-halogenoalkylamino comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₆-alkylamino, C₂-C₆-alkenyl-C₁-C₆-alkylamino, C₂-C₆-alkynyl-C₁-C₆-alkylamino, halogeno-C₃-C₆-cycloalkylamino comprising up to 9 halogen atoms which can be the same or different, arylamino which can be substituted by up to 5 groups Q, benzylamino which can be substituted by up to 5 groups Q, an aryl-C₃-C₆-cycloalkyl which can be substituted by up to 5 groups Q.

More preferred compounds of formula (I) according to the invention are those wherein R⁶ represents hydrogen, OH, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-halogenoalkyl comprising up to 5 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₂-alkyl, halogeno-C₃-C₆-cycloalkyl comprising up to 5 halogen atoms which can be the same or different, cyclohexenyl, C₁-C₂-alkoxy-C₁-C₂-alkyl, C₁-C₂-halogenoalkoxy-C₁-C₂-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₂-alkylsulfanyl-C₁-C₂-alkyl, C₁-C₄ trialkylsilyl C₁-C₂ alkyl, C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy comprising up to 5 halogen atoms which can be the same or different, alkenyl-C₁-C₄-alkoxy, C₂-C₄-alkynyl-C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-alkylsulfanyl-C₁-C₄-alkoxy, C₁-C₄-alkylamino-C₁-C₄-alkoxy, C₁-C₄-halogenoalkylamino-C₁-C₄-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₄-cycloalkylamino-C₁-C₄-alkoxy, C₁-C₄ trialkylsilyl C₁-C₄ alkoxy, phenyloxy which can be substituted by up to 5 groups Q, benzyloxy which can be substituted by up to 5 groups Q; C₁-C₄-alkylamino, Acetylamino, C₁-C₄-halogenoalkylamino comprising up to 9 halogen atoms which can be the same or different, C₂-C₄-alkenyl-C₁-C₄-alkylamino, C₂-C₄-alkynyl-C₁-C₄-alkylamino, phenylamino which can be substituted by up to 5 groups Q, benzylamino which can be substituted by up to 5 groups Q.

Preferred compounds of formula (I) according to the invention are those wherein R⁷ represents hydrogen, CN, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, halogeno-C₃-C₆-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-halogenoalkoxy-C₁-C₆-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulfanyl-C₁-C₆-alkyl, C₁-C₆-trialkylsilyl-C₁-C₆-alkyl, phenyl or naphthyl, each of which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q, phenyl-C₁-C₂-alkylimino.

More preferred compounds of formula (I) according to the invention are those wherein R⁷ represents hydrogen, CN, methyl, ethyl, n-propyl, isopropyl, n-, s- or t-butyl, trifluoromethyl, cyclohexenyl, vinyl, allyl propargyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, halogeno-C₃-C₄-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, phenyl or naphthyl, each of which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q.

Preferred compounds of formula (I) according to the invention are those wherein R⁸ represents hydrogen, OH, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₂-C₆-alkenyl-C₁-C₆-alkyl, C₂-C₆-alkynyl-C₁-C₆-alkyl, C₁-C₆-halogeno-C₃-C₆-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₆-cycloalkoxy-C₁-C₆-alkyl, C₁-C₆-halogenoalkoxy-C₁-C₆-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulfanyl-C₁-C₆-alkyl, C₁-C₆-alkylamino-C₁-C₆-alkyl, C₁-C₆-halogenoalkylamino-C₁-C₆-alkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkylamino-C₁-C₆-alkyl, C₁-C₆-trialkylsilyl-C₁-C₆-alkyl, phenyl which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q, C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy, C₁-C₆-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₆-alkoxy, C₂-C₆-alkenyl-C₁-C₆-alkoxy, C₂-C₆-alkynyl-C₁-C₆-alkoxy, C₁-C₆-halogeno-C₃-C₆-cycloalkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkenyloxy, C₁-C₆-alkoxy-C₁-C₆-alkoxy, C₃-C₅-cycloalkoxy-C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy-C₁-C₆-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulfanyl-C₁-C₆-alkoxy, C₁-C₆-alkylamino-C₁-C₆-alkoxy, C₁-C₆-halogenoalkylamino-C₁-C₆-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkylamino-C₁-C₆-alkoxy, C₁-C₆-trialkylsilyl-C₁-C₆-alkoxy, aryloxy which can be substituted by up to 5 groups Q, benzyloxy which can be substituted by up to 5 groups Q.

More preferred compounds of formula (I) according to the invention are those wherein R⁸ represents hydrogen, OH, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₂-halogenoalkyl comprising up to 5 halogen atoms which can be the same or different, cyclohexenyl, phenyl which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q, C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy comprising up to 5 halogen atoms which can be the same or different, alkenyl-C₁-C₄-alkoxy, C₂-C₄-alkynyl-C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-alkylsulfanyl-C₁-C₄-alkoxy, C₁-C₄-alkylamino-C₁-C₄-alkoxy, C₁-C₄-halogenoalkylamino-C₁-C₄-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₄-cycloalkylamino-C₁-C₄-alkoxy, C₁-C₄-trialkylsilyl-C₁-C₄-alkoxy, phenyloxy which can be substituted by up to 5 groups Q, benzyloxy which can be substituted by up to 5 groups Q.

Preferred compounds of formula (I) according to the invention are those wherein R⁹ represents hydrogen, OH, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₂-C₆-alkenyl-C₁-C₆-alkyl, C₂-C₆-alkynyl-C₁-C₆-alkyl, C₃-C₆-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₆-cycloalkoxy-C₁-C₆-alkyl, C₁-C₆-halogenoalkoxy-C₁-C₆-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulfanyl-C₁-C₆-alkyl, C₁-C₆-alkylamino-C₁-C₆-alkyl, C₁-C₆-halogenoalkylamino-C₁-C₆-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-trialkylsilyl-C₁-C₆-alkyl, phenyl which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q; C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy, C₁-C₆-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₆-alkoxy, C₂-C₆-alkenyl-C₁-C₆-alkoxy, C₂-C₆-alkynyl-C₁-C₈-alkoxy, halogeno-C₃-C₆-cycloalkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkenyloxy, C₁-C₆-alkoxy-C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy-C₁-C₆-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulfanyl-C₁-C₆-alkoxy, C₁-C₆-alkylamino-C₁-C₆-alkoxy, C₁-C₆-halogenoalkylamino-C₁-C₆-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-trialkylsilyl-C₁-C₆-alkoxy, phenyloxy which can be substituted by up to 5 groups Q, benzyloxy which can be substituted by up to 5 groups Q.

More preferred compounds of formula (I) according to the invention are those wherein R⁹ represents hydrogen, OH, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₂-halogenoalkyl comprising up to 5 halogen atoms which can be the same or different, cyclohexenyl, phenyl which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q; C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, phenoxy which can be substituted by up to 5 groups Q, benzyloxy which can be substituted by up to 5 groups Q.

Preferred compounds of formula (I) according to the invention are those wherein Q which can be the same or different, independently represents halogen, CN, NO₂, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylsulfanyl, C₁-C₆-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or, tri(C₁-C₆)alkylsilyl or tri(C₁-C₆)alkylsilyl-C₁-C₆-alkyl.

More preferred compounds of formula (I) according to the invention are those wherein Q which can be the same or different, independently represents fluorine, chlorine, bromine, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylsulfanyl, C₁-C₄-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, tri(C₁-C₄)alkylsilyl or tri(C₁-C₄)alkylsilyl-C₁-C₄-alkyl.

Preferred compounds of formula (I) according to the invention are those wherein R represents R^(B), wherein

-   t represents 1 -   Y² represents S or O -   Y³ represents S or O, -   Y⁴ represents O, S or NR⁹, -   R⁷ and R⁹ are as herein defined.

Preferred compounds of formula (I) according to the invention are those wherein R represents R^(B), wherein

-   t represents 1, -   Y² represents O -   Y³ represents O, -   Y⁴ represents O or NR⁹, -   R⁷ and R⁹ are as herein defined.

Preferred compounds of formula (I) according to the invention are those wherein R represents R^(B), wherein

-   t represents 1, -   Y² represents O -   Y³ represents O, -   Y⁴ represents NR⁹, -   R⁷ and R⁹ are as herein defined.

Preferred compounds of formula (I) according to the invention are those wherein R represents R^(B), wherein

-   t represents O, -   Y³ represents O or S, -   Y⁴ represents O, S or NR⁹, -   R⁷ is as herein defined, -   R⁹ represents hydrogen, C₁-C₈-alkyl, C₃-C₈-cycloalkyl,     C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be     the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl,     C₂-C₄-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl,     C₁-C₈-halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms     which can be the same or different, C₃-C₈-cycloalkenyl,     C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl,     C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms     which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl,     C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl     comprising up to 9 halogen atoms which can be the same or different,     C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl,     phenyl which can be substituted by up to 5 groups Q, benzyl which     can be substituted by up to 5 groups Q.

Preferred compounds of formula (I) according to the invention are those wherein R represents R^(B), wherein

-   t represents O, -   Y³ represents O, -   Y⁴ represents O or NR⁹, -   R⁷ is as herein defined, -   R⁹ represents hydrogen, C₁-C₈-alkyl, C₃-C₈-cycloalkyl,     C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be     the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl,     C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl,     C₁-C₈-halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms     which can be the same or different, C₃-C₈-cycloalkenyl,     C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl,     C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms     which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl,     C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl     comprising up to 9 halogen atoms which can be the same or different,     C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl,     phenyl which can be substituted by up to 5 groups Q, benzyl which     can be substituted by up to 5 groups Q.

Preferred compounds of formula (I) according to the invention are those wherein R represents R^(B), wherein

-   t represents O, -   Y³ represents O, -   Y⁴ represents NR⁹, -   R⁷ is as herein defined, -   R⁹ represents hydrogen, C₁-C₈-alkyl, C₃-C₈-cycloalkyl,     C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be     the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl,     C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl,     C₁-C₈-halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms     which can be the same or different, C₃-C₈-cycloalkenyl,     C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl,     C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms     which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl,     C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl     comprising up to 9 halogen atoms which can be the same or different,     C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl,     phenyl which can be substituted by up to 5 groups Q, benzyl which     can be substituted by up to 5 groups Q.

Preferred compounds according to the invention are those, wherein R represents R^(A)

Preferred compounds according to the invention are those, wherein R represents R^(B)

However, the general or preferred radical definitions or illustrations given above can also be combined with one another as desired, i.e. including combinations between respective ranges and preferred ranges. They apply both to the end products and, correspondingly, to precursors and intermediates. Moreover, individual definitions may not apply.

Preference is given to using those compounds of the formula (I) in which all radicals each have the meanings mentioned above as being preferred.

Particular preference is given to using those compounds of the formula (I) in which all radicals each have the meanings mentioned above as being more preferred.

Very particular preference is given to using those compounds of the formula (I) in which all radicals each have the meanings mentioned above as being even more preferred.

In these combinations of preferred features of the substituents of the compounds according to the invention, the said preferred features can also be selected among the more preferred features of each of R¹, R², R³, R⁴, n, Y¹, Y² and Het, so as to form most preferred subclasses of compounds according to the invention.

According to the invention, the following generic terms are generally used with the following meanings:

Halogen means fluorine, chlorine, bromine or iodine.

Heteroatom can be nitrogen, oxygen or sulphur.

Alkyl: saturated straight-chain or branched hydrocarbon radicals having 1 to 8 carbon atoms, for example C₁-C₆-alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl; heptyl, octyl.

Haloalkyl: straight-chain or branched alkyl groups having 1 to 8 carbon atoms (as mentioned above), where in these groups some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, for example C₁-C₃-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl.

Alkenyl: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 8 carbon atoms and a double bond in any position, for example C₂-C₆-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.

Alkynyl: straight-chain or branched hydrocarbon groups having 2 to 8 carbon atoms and a triple bond in any position, for example C₂-C₆-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl.

Cycloalkyl: monocyclic saturated hydrocarbon groups having 3 to 8 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.

Cycloalkenyl: monocyclic nonaromatic hydrocarbon groups having 3 to 8 carbon ring members and at least one double bond, such as cyclopenten-1-yl, cyclohexen-1-yl, cyclohepta-1,3-dien-1-yl.

Alkoxycarbonyl: an alkoxy group having 1 to 6 carbon atoms (as mentioned above) which is attached to the skeleton via a carbonyl group (—CO—).

The present invention also relates to a process for the preparation of compounds of formula (I). Thus, according to a further aspect of the present invention, there is provided a process P1 for the preparation of compounds of formula (I), as herein-defined, as illustrated by the following reaction schemes. If not stated otherwise all radicals have the meanings as defined above.

According to the invention process P1 may be performed if appropriate in the presence of a solvent, if appropriate in the presence of a catalyst and if appropriate in the presence of a base.

Compounds of formula (III) are commercially available or prepared from known procedures such as reductive amination of carbonyls, nucleophilic displacement, and reduction of amides, cyanides, oximes or nitro groups (cf. R. C. Larock Comprehensive organic transformations, 1989, VCH publishers).

The present invention also relates to a process for the preparation of compounds of formula (I-c) and (I-d).

Thus, according to a further aspect of the present invention, there is provided a process P2 for the preparation of compounds of formula (I-c) and (I-d), as herein-defined, as illustrated by the following reaction scheme:

In Step 1 the carboxylic acid-protecting group is cleaved according to known methods (cf. T. W. Greene and P. G. M. Wuts, Protective Group in Organic Chemistry, 3^(rd) ed., John Wiley & Sons).

According to the invention, Step 2 of process P2 may be performed if appropriate in the presence of a solvent, if appropriate in the presence of a base and if appropriate in the presence of a condensing reagent or a catalyst.

Suitable condensing reagents for carrying out Step 2 of process P2 according to the invention may be chosen as being acid halide former, such as phosgene, phosphorous tri-bromide, phosphorous trichloride, phosphorous pentachloride, phosphorous trichloride oxide or thionyl chloride; anhydride former, such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; carbodiimides, such as N,N′-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorous pentoxide, polyphosphoric acid, N,N′-carbonyl-diimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine/tetrachloromethane, 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate or bromo-tripyrrolidino-phosphonium-hexafluorophosphate.

Suitable catalysts for carrying out Step 2 of process P2 according to the invention may be chosen as being 4-dimethyl-aminopyridine, 1-hydroxy-benzotriazole or dimethylformamide.

Compounds of formula (IV) could be prepared according to process P1.

Compounds of formula (V) are commercially available or prepared from known procedures such as reductive amination of carbonyls, nucleophilic displacement, and reduction of amides, cyanides or nitro groups (cf. R. C. Larock Comprehensive organic transformations, 1989, VCH publishers).

The present invention also relates to a process for the preparation of compounds of (I-e). Thus, according to a further aspect of the present invention, there is provided a process P3 for the preparation of compounds of formula (I-e), as herein-defined, as illustrated by the following reaction scheme:

According to the invention process P3 may be performed if appropriate in the presence of a solvent, if appropriate in the presence of a base and if appropriate in the presence of a condensing reagent or a catalyst.

Suitable condensing reagents for carrying process P3 according to the invention may be chosen as being a Lewis acid such as for example MgCl₂, MgBr₂, AlMe₃, AlEt₃, AlCl₃, AlBr₃, ZnCl₂, ZnBr₂, SnCl₄, TiCl₄ or complex thereof such as, amongst others, MgBr₂.Et₂O, ZnCl₂.Et₂O, AlMe₃.DABCO, AlCl₃.THF.

The present invention also relates to a process for the preparation of compounds of formula (I-g). Thus, according to a further aspect of the present invention, there is provided a process P4 for the preparation of compounds of formula (I-g), as herein-defined, as illustrated by the following reaction scheme:

Compound (VIII) can be prepared according to known methods either in situ or prior to the reaction.

Compounds of formula (I-f) can be prepared according to process P1.

Suitable catalyst for carrying out processes P1, P4 according to the invention may be chosen from metal salt or complex. Suitable metal derivatives for this purpose are based on palladium. Suitable metal salts or complexes for this purpose are palladium chloride, palladium acetate, tetrakis(triphenylphosphine)palladium, bis(triphenylphosphine)palladium dichloride or 1,1′-bis(diphenylphosphino) ferrocenepalladium(II) chloride.

It is also possible to generate a palladium complex in the reaction mixture by separate addition to the reaction of a palladium salt and a ligand or salt, such as a phosphine, for example triethylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine, 2-(dicyclohexylphosphine)biphenyl, 2-(di-tert-butylphosphin)biphenyl, 2-(dicyclohexylphosphine)-2′-(N,N-dimethylamino)-biphenyl, triphenylphosphine, tris-(o-tolyl)phosphine, sodium 3-(diphenylphosphino)benzolsulfonate, tris-2-(methoxyphenyl)phosphine, 2,2′-bis-(diphenylphosphine)-1,1′-binaphthyl, 1,4-bis-(diphenylphosphine)butane, 1,2-bis-(diphenylphosphine)ethane, 1,4-bis-(dicyclohexylphosphine)butane, 1,2-bis-(dicyclohexylphosphine)ethane, 2-(dicyclohexylphosphine)-2′-(N,N-dimethylamino)-biphenyl, bis(diphenylphosphino)ferrocene, tris-(2,4-tert-butylphenyl)-phosphite, (R)-(−)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine, (S)-(+)-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine, (R)-(−)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine, (S)-(+)-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethyldi-t-butylphosphine or 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride.

It is also advantageous to choose the appropriate catalyst and/or ligand from commercial catalogues such as “Metal Catalysts for Organic Synthesis” by Strem Chemicals or “Phosphorous Ligands and Compounds” by Strem Chemicals.

The present invention also relates to a process for the preparation of compounds of formula (I-i). Thus, according to a further aspect of the present invention, there is provided a process P5 for the preparation of compounds of formula (I-i), as herein-defined, as illustrated by the following reaction scheme:

According to the invention, process P5 may be performed if appropriate in the presence of a solvent, if appropriate in the presence of a base and in the presence of a thionating agent.

Suitable thionating agents for carrying out process P5 according to the invention can be sulphur (S), sulfhydric acid (H₂₅), sodium sulfide (Na₂S), sodium hydrosulfide (NaHS), boron trisulfide (B₂S₃), bis(diethylaluminium) sulfide [(AlEt₂)₂S], ammonium sulfide [(NH₄)₂S], phosphorous pentasulfide (P₂S₅), Lawesson's reagent [2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiadiphosphetane 2,4-disulfide] or a polymer-supported thionating reagent (cf. J. Chem. Soc. Perkin 1, 2001, 358).

The present invention also relates to a process for the preparation of compounds of formula (I-j). Thus, according to a further aspect of the present invention, there is provided a process P6 for the preparation of compounds of formula (I-j), as herein-defined, as illustrated by the following reaction scheme:

According to the invention, process P6 may be performed if appropriate in the presence of a solvent and if appropriate in the presence of a base.

Compounds of formula (X) are commercially available or can be prepared according to known methods.

The present invention also relates to a process for the preparation of compounds of formula (I-k). Thus, according to a further aspect of the present invention, there is provided a process P7 for the preparation of compounds of formula (I-k), as herein-defined, as illustrated by the following reaction scheme:

According to the invention, process P7 may be performed if appropriate in the presence of a solvent and if appropriate in the presence of a base.

Compounds of formula (XI) are commercially available or can be prepared according to known methods.

Compounds of formula (II), useful as synthetic intermediates, could be prepared according to process P8 as illustrated by the following reaction scheme:

According to the invention, suitable reagents to perform process P8 may be chosen from the following groups:

-   -   provided that Y⁶ represents an oxygen atom:         phosphorous(V)oxychloride, phosphorous(V)oxybromide, phosphorous         pentachloride, thionyl chloride, thionyl bromide, diazomethane,         methylbromide, methyliodide, methyltriflate, carbon         tetrachloride and triphenylphosphine, carbon tetrabromide and         triphenylphosphine, N-chlorosuccinimide and triphenylphosphine,         N-bromosuccinimide and triphenylphosphine, N-iodosuccinimide and         triphenylphosphine, triflic anhydride, methanesulfonyl chloride,         p-tolylsulfonylchloride, sulfuryl chloride, sulfuryl bromide,         chlorine, phosgene, triphosgene, oxalyl chloride.     -   provided that Y⁶ represents a sulphur atom: methyliodide,         methylbromide, methylchloride, methyltrifluoromethanesulfonate,         dimethylsulfate.

According to the invention process P8 may be performed if appropriate in the presence of a solvent and if appropriate in the presence of a base.

Compounds of formula (XII) are prepared from known procedures such as condensation of a malonic derivative with an activated carboxylic acid (cf. Perez M. A., Soto J. L. Journal of heterocyclic chemistry, 1982, 19(1), 177-179)

Compounds of formula (XII) may exist in Z-form or in E-form when they are present in enol-form, where the correct assignment of Z and E according to the IUPAC nomenclature depends on the definitions of the different substituents. For easy reference in this patent application the assignment is made as shown. In all formulas below and above the E-form is used. Nevertheless the Z-form is also part of this invention. In addition compounds of formula (XII) may exist in keto-form.

Compounds of formula (IX), useful as synthetic intermediates, could be prepared according to process P9 as illustrated by the following reaction scheme:

According to the invention process P9 may be performed if appropriate in the presence of a solvent, if appropriate in the presence of a catalyst and if appropriate in the presence of a base.

Compounds of formula (IX) may exist in Z-form or in E-form where the correct assignment of Z and E according to the IUPAC nomenclature depends on the definitions of the different substituents

Compounds of formula (XIII), useful as synthetic intermediates, could be prepared according to process P9 as illustrated by the following reaction scheme:

According to the invention process P10 may be performed if appropriate in the presence of a solvent.

Compounds of formula (XIII) may exist in Z-form or in E-form where the correct assignment of Z and E according to the IUPAC nomenclature depends on the definitions of the different substituents Compounds of formula (XIV) are commercially available or prepared from known procedures such as alkylation of corresponding Weinreb amides or oxidation of alcohols (cf. R. C. Larock Comprehensive organic transformations, 1989, VCH publishers).

The Vilsmeier reagent can be prepared by mixing an activating reagent such as for example SOCl₂, SOBr₂, POCl₃, POBr₃, PCl₅, PBr₅, (COCl)₂, COCl₂ with a N,N-dialkylformamide such as for example DMF either in situ or prior to the reaction.

A crossed double bond in the formulae above means that either cis or trans configuration may be present as shown in the following example:

Suitable solvents for carrying out processes P1, P2, P3, P4, P5, P6, P7, P8, P9 and P10 according to the invention are customary inert organic solvents. Preference is given to using optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichlorethane or trichlorethane, ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, nitriles, such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile, amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide, esters, such as methyl acetate or ethyl acetate, sulphoxides, such as dimethyl sulphoxide, or sulphones, such as sulpholane.

Suitable bases for carrying out processes P1, P2, P3, P4, P5, P6, P7, P8, P9 and P10 according to the invention are inorganic and organic bases which are customary for such reactions. Preference is given to using alkaline earth metal, alkali metal hydride, alkali metal hydroxides or alkali metal alkoxides, such as sodium hydroxide, sodium hydride, calcium hydroxide, potassium hydroxide, potassium tert-butoxide or other ammonium hydroxide, alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, cesium carbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate, and also tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

It is also possible to employ the reaction components in other ratios. Work-up is carried out by known methods.

In general, the reaction mixture is concentrated under reduced pressure. The residue that remains can be freed by known methods, such as chromatography or recrystallization, from any impurities that can still be present.

When carrying out processes P1, P2, P3, P4, P5, P6, P7, P8, P9 and P10 according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, these processes are carried out at temperatures from 0° C. to 160° C., preferably from 10° C. to 120° C. A way to control the temperature for the processes according to the invention is to use micro-wave technology.

Processes P1, P2, P3, P4, P5, P6, P7, P8, P9 and P10 according to the invention are generally carried out under atmospheric pressure. It is also possible to operate under elevated or reduced pressure.

Compounds according to the invention can be prepared according to the above described processes. It will nevertheless be understood that, on the basis of his general knowledge and of available publications, the skilled worker will be able to adapt these processes according to the specifics of each of the compounds according to the invention that is desired to be synthesized.

The present invention furthermore relates to compositions for combating/controlling undesirable microorganisms comprising the active compounds according to the invention. Preferably, the compositions are fungicidal compositions comprising agriculturally suitable auxiliaries, solvents, carriers, surfactants or extenders.

Furthermore the invention relates to a method of combating undesirable microorganisms, characterized in that the compounds according to the invention are applied to the phytopathogenic fungi and/or their habitat.

According to the invention, carrier is to be understood as meaning a natural or synthetic, organic or inorganic substance which is mixed or combined with the active compounds for better applicability, in particular for application to plants or plant parts or seeds. The carrier, which may be solid or liquid is generally inert and should be suitable for use in agriculture.

Suitable solid or liquid carriers are: for example ammonium salts and natural ground minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral oils and vegetable oils, and also derivatives thereof. It is also possible to use mixtures of such carriers. Solid carriers suitable for granules are: for example crushed and fractionated natural minerals, such as calcite, marble, pumice, sepiolite, dolomite, and also synthetic granules of inorganic and organic meals and also granules of organic material, such as sawdust, coconut shells, maize cobs and tobacco stalks.

Suitable liquefied gaseous extenders or carriers are liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants, such as butane, propane, nitrogen and carbon dioxide.

Tackifiers, such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules and latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, or else natural phospholipids, such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils and waxes, optionally modified.

If the extender used is water, it is also possible for example, to use organic solvents as auxiliary solvents. Suitable liquid solvents are essentially: aromatic compounds, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and also ethers and esters thereof, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and also water.

The compositions according to the invention may comprise additional further components, such as, for example, surfactants. Suitable surfactants are emulsifiers, dispersants or wetting agents having ionic or non-ionic properties, or mixtures of these surfactants. Examples of these are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates. The presence of a surfactant is required if one of the active compounds and/or one of the inert carriers is insoluble in water and when the application takes place in water. The proportion of surfactants is between 5 and 40 percent by weight of the composition according to the invention.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide, Prussian blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

If appropriate, other additional components may also be present, for example protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, stabilizers, sequestering agents, complex formers. In general, the active compounds can be combined with any solid or liquid additive customarily used for formulation purposes.

In general, the compositions according to the invention comprise between 0.05 and 99 percent by weight, 0.01 and 98 percent by weight, preferable between 0.1 and 95 percent by weight, particularly preferred between 0.5 and 90 percent by weight of the active compound according to the invention, very particularly preferable between 10 and 70 percent by weight.

The active compound combinations or compositions according to the invention can be used as such or, depending on their respective physical and/or chemical properties, in the form of their formulations or the use forms prepared therefrom, such as aerosols, capsule suspensions, cold-fogging concentrates, warm-fogging concentrates, encapsulated granules, fine granules, flowable concentrates for the treatment of seed, ready-to-use solutions, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, macrogranules, microgranules, oil-dispersible powders, oil-miscible flowable concentrates, oil-miscible liquids, foams, pastes, pesticide-coated seed, suspension concentrates, suspoemulsion concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, dusts and granules, water-soluble granules or tablets, water-soluble powders for the treatment of seed, wettable powders, natural products and synthetic substances impregnated with active compound, and also microencapsulations in polymeric substances and in coating materials for seed, and also ULV cold-fogging and warm-fogging formulations.

The formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds or the active compound combinations with at least one additive. Suitable additives are all customary formulation auxiliaries, such as, for example, organic solvents, extenders, solvents or diluents, solid carriers and fillers, surfactants (such as adjuvants, emulsifiers, dispersants, protective colloids, wetting agents and tackifiers), dispersants and/or binders or fixatives, preservatives, dyes and pigments, defoamers, inorganic and organic thickeners, water repellents, if appropriate siccatives and UV stabilizers, gibberellins and also water and further processing auxiliaries. Depending on the formulation type to be prepared in each case, further processing steps such as, for example, wet grinding, dry grinding or granulation may be required.

The compositions according to the invention do not only comprise ready-to-use compositions which can be applied with suitable apparatus to the plant or the seed, but also commercial concentrates which have to be diluted with water prior to use.

The active compound combinations according to the invention can be present in (commercial) formulations and in the use forms prepared from these formulations as a mixture with other (known) active compounds, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners and Semiochemicals.

The treatment according to the invention of the plants and plant parts with the active compounds or compositions is carried out directly or by action on their surroundings, habitat or storage space using customary treatment methods, for example by dipping, spraying, atomizing, irrigating, evaporating, dusting, fogging, broadcasting, foaming, painting, spreading-on, watering (drenching), drip irrigating and, in the case of propagation material, in particular in the case of seeds, furthermore as a powder for dry seed treatment, a solution for seed treatment, a water-soluble powder for slurry treatment, by incrusting, by coating with one or more layers, etc. It is furthermore possible to apply the active compounds by the ultra-low volume method, or to inject the active compound preparation or the active compound itself into the soil.

The invention furthermore comprises a method for treating seed. The invention furthermore relates to seed treated according to one of the methods described in the preceding paragraph.

The active compounds or compositions according to the invention are especially suitable for treating seed. A large part of the damage to crop plants caused by harmful organisms is triggered by an infection of the seed during storage or after sowing as well as during and after germination of the plant. This phase is particularly critical since the roots and shoots of the growing plant are particularly sensitive, and even small damage may result in the death of the plant. Accordingly, there is great interest in protecting the seed and the germinating plant by using appropriate compositions.

The control of phytopathogenic fungi by treating the seed of plants has been known for a long time and is the subject of continuous improvements. However, the treatment of seed entails a series of problems which cannot always be solved in a satisfactory manner. Thus, it is desirable to develop methods for protecting the seed and the germinating plant which dispense with the additional application of crop protection agents after sowing or after the emergence of the plants or which at least considerably reduce additional application. It is furthermore desirable to optimize the amount of active compound employed in such a way as to provide maximum protection for the seed and the germinating plant from attack by phytopathogenic fungi, but without damaging the plant itself by the active compound employed. In particular, methods for the treatment of seed should also take into consideration the intrinsic fungicidal properties of transgenic plants in order to achieve optimum protection of the seed and the germinating plant with a minimum of crop protection agents being employed.

Accordingly, the present invention also relates in particular to a method for protecting seed and germinating plants against attack by phytopathogenic fungi by treating the seed with a composition according to the invention. The invention also relates to the use of the compositions according to the invention for treating seed for protecting the seed and the germinating plant against phytopathogenic fungi. Furthermore, the invention relates to seed treated with a composition according to the invention for protection against phytopathogenic fungi.

The control of phytopathogenic fungi which damage plants post-emergence is carried out primarily by treating the soil and the above-ground parts of plants with crop protection compositions. Owing to the concerns regarding a possible impact of the crop protection composition on the environment and the health of humans and animals, there are efforts to reduce the amount of active compounds applied.

One of the advantages of the present invention is that, because of the particular systemic properties of the compositions according to the invention, treatment of the seed with these compositions not only protects the seed itself, but also the resulting plants after emergence, from phytopathogenic fungi. In this manner, the immediate treatment of the crop at the time of sowing or shortly thereafter can be dispensed with.

It is also considered to be advantageous that the mixtures according to the invention can be used in particular also for transgenic seed where the plant growing from this seed is capable of expressing a protein which acts against pests. By treating such seed with the active compound combinations or compositions according to the invention, even by the expression of the, for example, insecticidal protein, certain pests may be controlled. Surprisingly, a further synergistic effect may be observed here, which additionally increases the effectiveness of the protection against attack by pests.

The compositions according to the invention are suitable for protecting seed of any plant variety employed in agriculture, in the greenhouse, in forests or in horticulture or viticulture. In particular, this takes the form of seed of cereals (such as wheat, barley, rye, triticale, millet, oats), maize (corn), cotton, soya bean, rice, potatoes, sunflowers, beans, coffee, beets (e.g. sugar beets and fodder beets), peanuts, oilseed rape, poppies, olives, coconuts, cacao, sugar cane, tobacco, vegetables (such as tomatoes, cucumbers, onions and lettuce), lawn and ornamental plants (also see below). The treatment of seeds of cereals (such as wheat, barley, rye, triticale, and oats), maize (corn) and rice is of particular importance.

As also described further below, the treatment of transgenic seed with the active compound combinations or compositions according to the invention is of particular importance. This refers to the seed of plants containing at least one heterologous gene which allows the expression of a polypeptide or protein having insecticidal properties. The heterologous gene in transgenic seed can originate, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. Preferably, this heterologous gene is from Bacillus sp., the gene product having activity against the European corn borer and/or the Western corn rootworm. Particularly preferably, the heterologous gene originates from Bacillus thuringiensis.

In the context of the present invention, the active compound combinations or compositions according to the invention are applied on their own or in a suitable formulation to the seed. Preferably, the seed is treated in a state in which it is sufficiently stable so that the treatment does not cause any damage. In general, treatment of the seed may take place at any point in time between harvesting and sowing. Usually, the seed used is separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. Thus, it is possible to use, for example, seed which has been harvested, cleaned and dried to a moisture content of less than 15% by weight. Alternatively, it is also possible to use seed which, after drying, has been treated, for example, with water and then dried again.

When treating the seed, care must generally be taken that the amount of the composition according to the invention applied to the seed and/or the amount of further additives is chosen in such a way that the germination of the seed is not adversely affected, or that the resulting plant is not damaged. This must be borne in mind in particular in the case of active compounds which may have phytotoxic effects at certain application rates.

The compositions according to the invention can be applied directly, that is to say without comprising further components and without having been diluted. In general, it is preferable to apply the compositions to the seed in the form of a suitable formulation. Suitable formulations and methods for the treatment of seed are known to the person skilled in the art and are described, for example, in the following documents: U.S. Pat. No. 4,272,417, U.S. Pat. No. 4,245,432, U.S. Pat. No. 4,808,430, U.S. Pat. No. 5,876,739, US 2003/0176428 A, WO 2002/080675, WO 2002/028186.

The active compound combinations which can be used according to the invention can be converted into customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating materials for seed, and also ULV formulations.

These formulations are prepared in a known manner by mixing the active compounds or active compound combinations with customary additives, such as, for example, customary extenders and also solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and water as well.

Suitable colorants that may be present in the seed dressing formulations which can be used according to the invention include all colorants customary for such purposes. Use may be made both of pigments, of sparing solubility in water, and of dyes, which are soluble in water. Examples that may be mentioned include the colorants known under the designations Rhodamine B, C.I. Pigment Red 112, and C.I. Solvent Red 1.

Suitable wetting agents that may be present in the seed dressing formulations which can be used according to the invention include all substances which promote wetting and are customary in the formulation of active agrochemical substances. With preference it is possible to use alkylnaphthalene-sulphonates, such as diisopropyl- or diisobutylnaphthalene-sulphonates.

Suitable dispersants and/or emulsifiers that may be present in the seed dressing formulations which can be used according to the invention include all nonionic, anionic, and cationic dispersants which are customary in the formulation of active agrochemical substances. With preference, it is possible to use nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Particularly suitable nonionic dispersants are ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers, and tristyrylphenol polyglycol ethers, and their phosphated or sulphated derivatives. Particularly suitable anionic dispersants are lignosulphonates, polyacrylic salts, and arylsulphonate-formaldehyde condensates.

Defoamers that may be present in the seed dressing formulations to be used according to the invention include all foam-inhibiting compounds which are customary in the formulation of agrochemically active compounds. Preference is given to using silicone defoamers, magnesium stearate, silicone emulsions, long-chain alcohols, fatty acids and their salts and also organofluorine compounds and mixtures thereof.

Preservatives that may be present in the seed dressing formulations to be used according to the invention include all compounds which can be used for such purposes in agrochemical compositions. By way of example, mention may be made of dichlorophen and benzyl alcohol hemiformal.

Secondary thickeners that may be present in the seed dressing formulations to be used according to the invention include all compounds which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, polysaccharides, such as xanthan gum or Veegum, modified clays, phyllosilicates, such as attapulgite and bentonite, and also finely divided silicic acids.

Suitable adhesives that may be present in the seed dressing formulations to be used according to the invention include all customary binders which can be used in seed dressings. Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose may be mentioned as being preferred.

Suitable gibberellins that may be present in the seed dressing formulations to be used according to the invention are preferably the gibberellins A1, A3 (=gibberellic acid), A4 and A7; particular preference is given to using gibberellic acid. The gibberellins are known (cf. R. Wegler “Chemie der Pflanzenschutz- and Schädlingsbekämpfungsmittel” [Chemistry of Crop Protection Agents and Pesticides], Vol. 2, Springer Verlag, 1970, pp. 401-412).

The seed dressing formulations which can be used according to the invention may be used directly or after dilution with water beforehand to treat seed of any of a very wide variety of types. The seed dressing formulations which can be used according to the invention or their dilute preparations may also be used to dress seed of transgenic plants. In this context, synergistic effects may also arise in interaction with the substances formed by expression.

Suitable mixing equipment for treating seed with the seed dressing formulations which can be used according to the invention or the preparations prepared from them by adding water includes all mixing equipment which can commonly be used for dressing. The specific procedure adopted when dressing comprises introducing the seed into a mixer, adding the particular desired amount of seed dressing formulation, either as it is or following dilution with water beforehand, and carrying out mixing until the formulation is uniformly distributed on the seed. Optionally, a drying operation follows.

The active compounds or compositions according to the invention have strong microbicidal activity and can be used for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and material protection.

In crop protection, fungicides can be used for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

In crop protection, bactericides can be used for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

The fungicidal compositions according to the invention can be used for the curative or protective control of phytopathogenic fungi. Accordingly, the invention also relates to curative and protective methods for controlling phytopathogenic fungi using the active compound combinations or compositions according to the invention, which are applied to the seed, the plant or plant parts, the fruit or the soil in which the plants grow. Preference is given to application onto the plant or the plant parts, the fruits or the soil in which the plants grow.

The compositions according to the invention for combating phytopathogenic fungi in crop protection comprise an active, but non-phytotoxic amount of the compounds according to the invention. “Active, but non-phytotoxic amount” shall mean an amount of the composition according to the invention which is sufficient to control or to completely kill the plant disease caused by fungi, which amount at the same time does not exhibit noteworthy symptoms of phytotoxicity. These application rates generally may be varied in a broader range, which rate depends on several factors, e.g. the phytopathogenic fungi, the plant or crop, the climatic conditions and the ingredients of the composition according to the invention.

The fact that the active compounds, at the concentrations required for the controlling of plant diseases, are well tolerated by plants permits the treatment of aerial plant parts, of vegetative propagation material and seed, and of the soil.

According to the invention, it is possible to treat all plants and parts of plants. Plants are to be understood here as meaning all plants and plant populations, such as wanted and unwanted wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including plant cultivars which can or cannot be protected by plant variety protection rights. Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of the plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit bodies, fruits and seeds and also roots, tubers and rhizomes. Plant parts also include harvested material and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds. Preference is given to the treatment of the plants and the above-ground and below-ground parts and organs of the plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, and fruits.

The active compounds of the invention, in combination with good plant tolerance and favourable toxicity to warm-blooded animals and being tolerated well by the environment, are suitable for protecting plants and plant organs, for increasing the harvest yields, for improving the quality of the harvested material. They may be preferably employed as crop protection agents. They are active against normally sensitive and resistant species and against all or some stages of development.

The following plants may be mentioned as plants which can be treated according to the invention: cotton, flax, grapevines, fruit, vegetable, such as Rosaceae sp. (for example pomaceous fruit, such as apples and pears, but also stone fruit, such as apricots, cherries, almonds and peaches and soft fruit such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actimidaceae sp., Lauraceae sp., Musaceae sp. (for example banana trees and plantations), Rubiaceae sp. (for example coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example lemons, or anges and grapefruit), Solanaceae sp. (for example tomatoes), Liliaceae sp., Asteraceae sp. (for example lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumbers), Alliaceae sp. (for example leek, onions), Papilionaceae sp. (for example peas); major crop plants, such Gramineae sp. (for example maize, lawn, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (for example sunflowers), Brassicaceae sp. (for example white cabbage, red cabbage, broccoli, cauliflowers, Brussels sprouts, pak choi, kohlrabi, garden radish, and also oilseed rape, mustard, horseradish and cress), Fabacae sp. (for example beans, peas, peanuts), Papilionaceae sp. (for example soya beans), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example sugar beet, fodder beet, Swiss chard, beetroot); crop plants and ornamental plants in garden and forest; and also in each case genetically modified varieties of these plants.

As already mentioned above, it is possible to treat all plants and their parts according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms), and parts thereof are treated. The terms “parts”, “parts of plants” and “plant parts” have been explained above. Particularly preferably, plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention. Plant cultivars are to be understood as meaning plants having novel properties (“traits”) which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, bio- or genotypes.

The method of treatment according to the invention is used in the treatment of genetically modified organisms (GMOs), e.g. plants or seeds. Genetically modified plants (or transgenic plants) are plants of which a heterologous gene has been stably integrated into the genome. The expression “heterologous gene” essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloroplastic or mitochondrial genome gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by down regulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, co-suppression technology or RNA interference—RNAi-technology). A heterologous gene that is located in the genome is also called a transgene. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in super-additive (“synergistic”) effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the active compounds and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, bigger fruits, larger plant height, greener leaf color, earlier flowering, higher quality and/or a higher nutritional value of the harvested products, higher sugar concentration within the fruits, better storage stability and/or processability of the harvested products are possible, which exceed the effects which were actually to be expected.

At certain application rates, the active compound combinations according to the invention may also have a strengthening effect in plants. Accordingly, they are also suitable for mobilizing the defense system of the plant against attack by unwanted phytopathogenic fungi and/or microorganisms and/or viruses. This may, if appropriate, be one of the reasons of the enhanced activity of the combinations according to the invention, for example against fungi. Plant-strengthening (resistance-inducing) substances are to be understood as meaning, in the present context, those substances or combinations of substances which are capable of stimulating the defense system of plants in such a way that, when subsequently inoculated with unwanted phytopathogenic fungi and/or microorganisms and/or viruses, the treated plants display a substantial degree of resistance to these phytopathogenic fungi and/or microorganisms and/or viruses, Thus, the substances according to the invention can be employed for protecting plants against attack by the above-mentioned pathogens within a certain period of time after the treatment. The period of time within which protection is effected generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds.

Plants and plant cultivars which are preferably to be treated according to the invention include all plants which have genetic material which impart particularly advantageous, useful traits to these plants (whether obtained by breeding and/or biotechnological means).

Plants and plant cultivars which are also preferably to be treated according to the invention are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids.

Plants and plant cultivars which may also be treated according to the invention are those plants which are resistant to one or more abiotic stresses. Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozon exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.

Plants and plant cultivars which may also be treated according to the invention, are those plants characterized by enhanced yield characteristics. Increased yield in said plants can be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation. Yield can furthermore be affected by improved plant architecture (under stress and non-stress conditions), including but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance. Further yield traits include seed composition, such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction in anti-nutritional compounds, improved processability and better storage stability.

Plants that may be treated according to the invention are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stress factors. Such plants are typically made by crossing an inbred male-sterile parent line (the female parent) with another inbred male-fertile parent line (the male parent). Hybrid seed is typically harvested from the male sterile plants and sold to growers. Male sterile plants can sometimes (e.g. in corn) be produced by detasseling, i.e. the mechanical removal of the male reproductive organs (or males flowers) but, more typically, male sterility is the result of genetic determinants in the plant genome. In that case, and especially when seed is the desired product to be harvested from the hybrid plants it is typically useful to ensure that male fertility in the hybrid plants is fully restored. This can be accomplished by ensuring that the male parents have appropriate fertility restorer genes which are capable of restoring the male fertility in hybrid plants that contain the genetic determinants responsible for male-sterility. Genetic determinants for male sterility may be located in the cytoplasm. Examples of cytoplasmic male sterility (CMS) were for instance described in Brassica species. However, genetic determinants for male sterility can also be located in the nuclear genome. Male sterile plants can also be obtained by plant biotechnology methods such as genetic engineering. A particularly useful means of obtaining male-sterile plants is described in WO 89/10396 in which, for example, a ribonuclease such as barnase is selectively expressed in the tapetum cells in the stamens. Fertility can then be restored by expression in the tapetum cells of a ribonuclease inhibitor such as barstar.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance.

Herbicide-tolerant plants are for example glyphosate-tolerant plants, i.e. plants made tolerant to the herbicide glyphosate or salts thereof. Plants can be made tolerant to glyphosate through different means. For example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium, the CP4 gene of the bacterium Agrobacterium sp, the genes encoding a Petunia EPSPS, a Tomato EPSPS, or an Eleusine EPSPS. It can also be a mutated EPSPS. Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate oxido-reductase enzyme. Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate acetyl transferase enzyme. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the above-mentioned genes.

Other herbicide resistant plants are for example plants that are made tolerant to herbicides inhibiting the enzyme glutamine synthase, such as bialaphos, phosphinothricin or glufosinate. Such plants can be obtained by expressing an enzyme detoxifying the herbicide or a mutant glutamine synthase enzyme that is resistant to inhibition. One such efficient detoxifying enzyme is an enzyme encoding a phosphinothricin acetyltransferase (such as the bar or pat protein from Streptomyces species). Plants expressing an exogenous phosphinothricin acetyltransferase are also described.

Further herbicide-tolerant plants are also plants that are made tolerant to the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase (HPPD). Hydroxyphenylpyruvatedioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is transformed into homogentisate. Plants tolerant to HPPD-inhibitors can be transformed with a gene encoding a naturally-occurring resistant HPPD enzyme, or a gene encoding a mutated HPPD enzyme. Tolerance to HPPD-inhibitors can also be obtained by transforming plants with genes encoding certain enzymes enabling the formation of homogentisate despite the inhibition of the native HPPD enzyme by the HPPD-inhibitor. Tolerance of plants to HPPD inhibitors can also be improved by transforming plants with a gene encoding an enzyme prephenate dehydrogenase in addition to a gene encoding an HPPD-tolerant enzyme.

Still further herbicide resistant plants are plants that are made tolerant to acetolactate synthase (ALS) inhibitors. Known ALS-inhibitors include, for example, sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyoxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinone herbicides. Different mutations in the ALS enzyme (also known as acetohydroxy acid synthase, AHAS) are known to confer tolerance to different herbicides and groups of herbicides. The production of sulfonylurea-tolerant plants and imidazolinone-tolerant plants is described in WO 1996/033270. Other imidazolinone-tolerant plants are also described. Further sulfonylurea- and imidazolinone-tolerant plants are also described in for example WO 2007/024782.

Other plants tolerant to imidazolinone and/or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or mutation breeding as described for example for soybeans, for rice, for sugar beet, for lettuce, or for sunflower.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance.

An “insect-resistant transgenic plant”, as used herein, includes any plant containing at least one transgene comprising a coding sequence encoding:

-   1) an insecticidal crystal protein from Bacillus thuringiensis or an     insecticidal portion thereof, such as the insecticidal crystal     proteins listed online at:     http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/, or     insecticidal portions thereof, e.g., proteins of the Cry protein     classes Cry1Ab, Cry1Ac, Cry1F, Cry2Ab, Cry3Aa, or Cry3Bb or     insecticidal portions thereof; or -   2) a crystal protein from Bacillus thuringiensis or a portion     thereof which is insecticidal in the presence of a second other     crystal protein from Bacillus thuringiensis or a portion thereof,     such as the binary toxin made up of the Cry34 and Cry35 crystal     proteins; or -   3) a hybrid insecticidal protein comprising parts of different     insecticidal crystal proteins from Bacillus thuringiensis, such as a     hybrid of the proteins of 1) above or a hybrid of the proteins of 2)     above, e.g., the Cry1A.105 protein produced by corn event MON98034     (WO 2007/027777); or -   4) a protein of any one of 1) to 3) above wherein some, particularly     1 to 10, amino acids have been replaced by another amino acid to     obtain a higher insecticidal activity to a target insect species,     and/or to expand the range of target insect species affected, and/or     because of changes introduced into the encoding DNA during cloning     or transformation, such as the Cry3Bb1 protein in corn events MON863     or MON88017, or the Cry3A protein in corn event MIR604; -   5) an insecticidal secreted protein from Bacillus thuringiensis or     Bacillus cereus, or an insecticidal portion thereof, such as the     vegetative insecticidal (VIP) proteins listed at:     http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html,     e.g. proteins from the VIP3Aa protein class; or -   6) secreted protein from Bacillus thuringiensis or Bacillus cereus     which is insecticidal in the presence of a second secreted protein     from Bacillus thuringiensis or B. cereus, such as the binary toxin     made up of the VIP1A and VIP2A proteins; or -   7) hybrid insecticidal protein comprising parts from different     secreted proteins from Bacillus thuringiensis or Bacillus cereus,     such as a hybrid of the proteins in 1) above or a hybrid of the     proteins in 2) above; or -   8) protein of any one of 1) to 3) above wherein some, particularly 1     to 10, amino acids have been replaced by another amino acid to     obtain a higher insecticidal activity to a target insect species,     and/or to expand the range of target insect species affected, and/or     because of changes introduced into the encoding DNA during cloning     or transformation (while still encoding an insecticidal protein),     such as the VIP3Aa protein in cotton event COT102.

Of course, an insect-resistant transgenic plant, as used herein, also includes any plant comprising a combination of genes encoding the proteins of any one of the above classes 1 to 8. In one embodiment, an insect-resistant plant contains more than one transgene encoding a protein of any one of the above classes 1 to 8, to expand the range of target insect species affected when using different proteins directed at different target insect species, or to delay insect resistance development to the plants by using different proteins insecticidal to the same target insect species but having a different mode of action, such as binding to different receptor binding sites in the insect.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress resistance. Particularly useful stress tolerance plants include:

-   a. plants which contain a transgene capable of reducing the     expression and/or the activity of poly(ADP-ribose)polymerase (PARP)     gene in the plant cells or plants -   b. plants which contain a stress tolerance enhancing transgene     capable of reducing the expression and/or the activity of the PARG     encoding genes of the plants or plants cells. -   c. plants which contain a stress tolerance enhancing transgene     coding for a plant-functional enzyme of the nicotinamide adenine     dinucleotide salvage synthesis pathway including nicotinamidase,     nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide     adenyl transferase, nicotinamide adenine dinucleotide synthetase or     nicotine amide phosphorybosyltransferase.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention show altered quantity, quality and/or storage-stability of the harvested product and/or altered properties of specific ingredients of the harvested product such as:

-   1) transgenic plants which synthesize a modified starch, which in     its physical-chemical characteristics, in particular the amylose     content or the amylose/amylopectin ratio, the degree of branching,     the average chain length, the side chain distribution, the viscosity     behaviour, the gelling strength, the starch grain size and/or the     starch grain morphology, is changed in comparison with the     synthesised starch in wild type plant cells or plants, so that this     is better suited for special applications. -   2) transgenic plants which synthesize non starch carbohydrate     polymers or which synthesize non starch carbohydrate polymers with     altered properties in comparison to wild type plants without genetic     modification. Examples are plants producing polyfructose, especially     of the inulin and levan-type, plants producing alpha 1,4 glucans,     plants producing alpha-1,6 branched alpha-1,4-glucans, plants     producing alternan, -   3) transgenic plants which produce hyaluronan.

Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by genetic transformation or by selection of plants contain a mutation imparting such altered fiber characteristics and include:

-   a) Plants, such as cotton plants, containing an altered form of     cellulose synthase genes, -   b) Plants, such as cotton plants, containing an altered form of rsw2     or rsw3 homologous nucleic acids, -   c) Plants, such as cotton plants, with increased expression of     sucrose phosphate synthase, -   d) Plants, such as cotton plants, with increased expression of     sucrose synthase, -   e) Plants, such as cotton plants, wherein the timing of the     plasmodesmatal gating at the basis of the fiber cell is altered,     e.g. through downregulation of fiberselective β1,3-glucanase, -   f) Plants, such as cotton plants, having fibers with altered     reactivity, e.g. through the expression of     N-acteylglucosaminetransferase gene including nodC and     chitinsynthase genes.

Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered oil profile characteristics. Such plants can be obtained by genetic transformation or by selection of plants contain a mutation imparting such altered oil characteristics and include:

-   a) Plants, such as oilseed rape plants, producing oil having a high     oleic acid content, -   b) Plants such as oilseed rape plants, producing oil having a low     linolenic acid content, -   c) Plant such as oilseed rape plants, producing oil having a low     level of saturated fatty acids.

Particularly useful transgenic plants which may be treated according to the invention are plants which comprise one or more genes which encode one or more toxins, such as the following which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), BiteGard® (for example maize), Bt-Xtra® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example maize), Protecta® and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize).

Particularly useful transgenic plants which may be treated according to the invention are plants containing transformation events, or combination of transformation events, that are listed for example in the databases from various national or regional regulatory agencies (see for example http://gmoinfo.jrc.it/gmp_browse.aspx and http://www.agbios.com/dbase.php).

In material protection the substances of the invention may be used for the protection of technical materials against infestation and destruction by undesirable fungi and/or microorganisms.

Technical materials are understood to be in the present context non-living materials that have been prepared for use in engineering. For example, technical materials that are to be protected against microbiological change or destruction by the active materials of the invention can be adhesives, glues, paper and cardboard, textiles, carpets, leather, wood, paint and plastic articles, cooling lubricants and other materials that can be infested or destroyed by micro-organisms. Within the context of materials to be protected are also parts of production plants and buildings, for example cooling circuits, cooling and heating systems, air conditioning and ventilation systems, which can be adversely affected by the propagation of fungi and/or microorganisms. Within the context of the present invention, preferably mentioned as technical materials are adhesives, glues, paper and cardboard, leather, wood, paints, cooling lubricants and heat exchanger liquids, particularly preferred is wood. The combinations according to the invention can prevent disadvantageous effects like decaying, dis- and decoloring, or molding. The active compound combinations and compositions according to the invention can likewise be employed for protecting against colonization of objects, in particular ship hulls, sieves, nets, buildings, quays and signalling installations, which are in contact with sea water or brackish water.

The method of treatment according to the invention can also be used in the field of protecting storage goods against attack of fungi and microorganisms. According to the present invention, the term “storage goods” is understood to denote natural substances of vegetable or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired. Storage goods of vegetable origin, such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted. Also falling under the definition of storage goods is timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood. Storage goods of animal origin are hides, leather, furs, hairs and the like. The combinations according the present invention can prevent disadvantageous effects such as decay, discoloration or mold. Preferably “storage goods” is understood to denote natural substances of vegetable origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.

Some pathogens of fungal diseases which can be treated according to the invention may be mentioned by way of example, but not by way of limitation:

Diseases caused by powdery mildew pathogens, such as, for example, Blumeria species, such as, for example, Blumeria graminis; Podosphaera species, such as, for example, Podosphaera leucotricha; Sphaerotheca species, such as, for example, Sphaerotheca fuliginea; Uncinula species, such as, for example, Uncinula necator;

Diseases caused by rust disease pathogens, such as, for example, Gymnosporangium species, such as, for example, Gymnosporangium sabinae; Hemileia species, such as, for example, Hemileia vastatrix; Phakopsora species, such as, for example, Phakopsora pachyrhizi and Phakopsora meibomiae; Puccinia species, such as, for example, Puccinia recondita or Puccinia triticina; Uromyces species, such as, for example, Uromyces appendiculatus;

Diseases caused by pathogens from the group of the Oomycetes, such as, for example, Bremia species, such as, for example, Bremia lactucae; Peronospora species, such as, for example, Peronospora pisi or P. brassicae; Phytophthora species, such as, for example Phytophthora infestans; Plasmopara species, such as, for example, Plasmopara viticola; Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, such as, for example, Pythium ultimum;

Leaf blotch diseases and leaf wilt diseases caused, for example, by Alternaria species, such as, for example, Alternaria solani; Cercospora species, such as, for example, Cercospora beticola; Cladiosporium species, such as, for example, Cladiosporium cucumerinum; Cochliobolus species, such as, for example, Cochliobolus sativus (conidia form: Drechslera, Syn: Helminthosporium); Colletotrichum species, such as, for example, Colletotrichum lindemuthanium; Cycloconium species, such as, for example, Cycloconium oleaginum; Diaporthe species, such as, for example, Diaporthe citri; Elsinoe species, such as, for example, Elsinoe fawcettii; Gloeosporium species, such as, for example, Gloeosporium laeticolor; Glomerella species, such as, for example, Glomerella cingulata; Guignardia species, such as, for example, Guignardia bidwelli; Leptosphaeria species, such as, for example, Leptosphaeria maculans; Magnaporthe species, such as, for example, Magnaporthe grisea; Microdochium species, such as, for example, Microdochium nivale; Mycosphaerella species, such as, for example, Mycosphaerella graminicola and M. fijiensis; Phaeosphaeria species, such as, for example, Phaeosphaeria nodorum; Pyrenophora species, such as, for example, Pyrenophora teres; Ramularia species, such as, for example, Ramularia collo-cygni; Rhynchosporium species, such as, for example, Rhynchosporium secalis; Septoria species, such as, for example, Septoria apii; Typhula species, such as, for example, Typhula incamata; Venturia species, such as, for example, Venturia inaequalis;

Root and stem diseases caused, for example, by Corticium species, such as, for example, Corticium graminearum; Fusarium species, such as, for example, Fusarium oxysporum; Gaeumannomyces species, such as, for example, Gaeumannomyces graminis; Rhizoctonia species, such as, for example Rhizoctonia solani; Tapesia species, such as, for example, Tapesia acuformis; Thielaviopsis species, such as, for example, Thielaviopsis basicola;

Ear and panicle diseases (including maize cobs) caused, for example, by Alternaria species, such as, for example, Alternaria spp.; Aspergillus species, such as, for example, Aspergillus flavus; Cladosporium species, such as, for example, Cladosporium cladosporioides; Claviceps species, such as, for example, Claviceps purpurea; Fusarium species, such as, for example, Fusarium culmorum; Gibberella species, such as, for example, Gibberella zeae, Gibberella fujikuroi; Monographella species, such as, for example, Monographella nivalis; Septoria species, such as for example, Septoria nodorum;

Diseases caused by smut fungi, such as, for example, Sphacelotheca species, such as, for example, Sphacelotheca reiliana; Tilletia species, such as, for example, Tilletia caries; T. controversa; Urocystis species, such as, for example, Urocystis occulta; Ustilago species, such as, for example, Ustilago nuda; U. nuda tritici;

Fruit rot caused, for example, by Aspergillus species, such as, for example, Aspergillus flavus; Botrytis species, such as, for example, Botrytis cinerea; Penicillium species, such as, for example, Penicillium expansum and P. purpurogenum; Sclerotinia species, such as, for example, Sclerotinia sclerotionim; Verticilium species, such as, for example, Verticilium alboatrum;

Seed- and soil-home rot and wilt diseases, and also diseases of seedlings, caused, for example, by Fusarium species, such as, for example, Fusarium culmorum; Phytophthora species, such as, for example, Phytophthora cactorum; Pythium species, such as, for example, Pythium ultimum; Rhizoctonia species, such as, for example, Rhizoctonia solani; Sclerotium species, such as, for example, Sclerotium rolfsii;

Cancerous diseases, galls and witches' broom caused, for example, by Nectria species, such as, for example, Nectria galligena;

Wilt diseases caused, for example, by Monilinia species, such as, for example, Monilinia laxa;

Deformations of leaves, flowers and fruits caused, for example, by Taphrina species, such as, for example, Taphrina deformans;

Degenerative diseases of woody plants caused, for example, by Esca species, such as, for example, Phaemoniella clamydospora and Phaeoacremonium aleophilum and Fomitiporia mediterranea;

Diseases of flowers and seeds caused, for example, by Botrytis species, such as, for example, Botrytis cinerea;

Diseases of plant tubers caused, for example, by Rhizoctonia species, such as, for example, Rhizoctonia solani; Helminthosporium species, such as, for example, Helminthosporium solani;

Diseases caused by bacteriopathogens, such as, for example, Xanthomonas species, such as, for example, Xanthomonas campestris pv. oryzae; Pseudomonas species, such as, for example, Pseudomonas syringae pv. lachrymans; Erwinia species, such as, for example, Erwinia amylovora.

Preference is given to controlling the following diseases of soya beans:

fungal diseases on leaves, stems, pods and seeds caused, for example, by alternaria leaf spot (Alternaria spec. atrans tenuissima), anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), cercospora leaf spot and blight (Cercospora kikuchii), choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi Phakopsora meibomiae), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), target spot (Corynespora cassiicola).

Fungal diseases on roots and the stem base caused, for example, by black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), fusarium blight or wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmopspora vasinfecta), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidermaturn, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia Southern blight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).

It is also possible to control resistant strains of the organisms mentioned above.

Microorganisms capable of degrading or changing the industrial materials which may be mentioned are, for example, bacteria, fungi, yeasts, algae and slime organisms. The active compounds according to the invention preferably act against fungi, in particular moulds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae. Microorganisms of the following genera may be mentioned as examples: Alternaria, such as Alternaria tenuis, Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosum, Coniophora, such as Coniophora puetana, Lentinus, such as Lentinus tigrinus, Penicillium, such as Penicillium glaucum, Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans, Sclerophoma, such as Sclerophoma pityophila, Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aeruginosa, and Staphylococcus, such as Staphylococcus aureus.

In addition, the compounds of the formula (I) according to the invention also have very good antimycotic activity. They have a very broad antimycotic activity spectrum in particular against dermatophytes and yeasts, moulds and diphasic fungi (for example against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The list of these fungi by no means limits the mycotic spectrum which can be covered, but is only for illustration.

When applying the compounds according to the invention the application rates can be varied within a broad range. The dose of active compound/application rate usually applied in the method of treatment according to the invention is generally and advantageously

-   -   for treatment of part of plants, e.g. leafs (foliar treatment):         from 0.1 to 10,000 g/ha, preferably from 10 to 1,000 g/ha, more         preferably from 50 to 300 g/ha; in case of drench or drip         application, the dose can even be reduced, especially while         using inert substrates like rockwool or perlite;     -   for seed treatment: from 2 to 200 g per 100 kg of seed,         preferably from 3 to 150 g per 100 kg of seed, more preferably         from 2.5 to 25 g per 100 kg of seed, even more preferably from         2.5 to 12.5 g per 100 kg of seed;     -   for soil treatment: from 0.1 to 10,000 g/ha, preferably from 1         to 5,000 g/ha.

The doses herein indicated are given as illustrative examples of the method according to the invention. A person skilled in the art will know how to adapt the application doses, notably according to the nature of the plant or crop to be treated.

The combination according to the invention can be used in order to protect plants within a certain time range after the treatment against pests and/or phytopathogenic fungi and/or microorganisms. The time range, in which protection is effected, spans in general 1 to 28 days, preferably 1 to 14 days, more preferably 1 to 10 days, even more preferably 1 to 7 days after the treatment of the plants with the combinations or up to 200 days after the treatment of plant propagation material.

Furthermore combinations and compositions according to the invention may also be used to reduce the contents of mycotoxins in plants and the harvested plant material and therefore in foods and animal feed stuff made therefrom. Especially but not exclusively the following mycotoxins can be specified: Deoxynivalenole (DON), Nivalenole, 15-Ac-DON, 3-Ac-DON, T2-und HT2-Toxins, Fumonisines, Zearalenone Moniliformine, Fusarine, Diaceotoxyscirpenole (DAS), Beauvericine, Enniatine, Fusaroproliferine, Fusarenole, Ochratoxines, Patuline, Ergotalkaloides und Aflatoxins, which are caused for example by the following fungal diseases: Fusarium spec., like Fusarium acuminatum, F. avenaceum, F. crookwellense, F. culmorum, F. graminearum (Gibberella zeae), F. equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. proliferatum, F. poae, F. pseudograminearum, F. sambucinum, F. scirpi, F. semitectum, F. solani, F. sporotrichoides, F. langsethiae, F. subglutinans, F. tricinctum, F. verticillioides and others but also by Aspergillus spec., Penicillium spec., Claviceps purpurea, Stachybotrys spec. and others.

The invention is illustrated by the examples below. However, the invention is not limited to the examples.

PREPARATION EXAMPLES Examples of Process P1

To a solution of ethyl 3-chloro-3-(2-chloropyridin-3-yl)-2-cyanoacrylate (0.3 g, 1.10 mmol, 1 eq.) in 5 ml of tetrahydrofuran was added propylamine (0.131 g, 2.21 mmol, 2 eq.) at room temperature. After being stirred for 8 h at 80° C., the mixture was evaporated. The residue was diluted with AcOEt and the precipitate was filtered off. The filtrate was evaporated and the residual oil was subjected to column chromatography to give ethyl (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-3-(propylamino)acrylate (0.240 g, 74% yield).

¹H-NMR (400 MHz, CDCl₃/CDCl₃=7.26): 9.96 (bs, 1H), 8.55-8.58 (m, 1H), 7.67-7.71 (m, 1H), 7.39-7.44 (m, 3H), 7.39-7.50 (m, 3H), 4.27 (q, 2H), 3.08-3.14 (m, 1H), 2.88-2.94 (m, 1H), 1.35-1.63 (m, 2H), 1.32 (t, 3H), 0.92 (t, 3H).

To a solution of ethyl 3-chloro-3-(2-chloropyridin-3-yl)-2-cyanoacrylate (0.2 g, 0.738 mmol, 1 eq.) in 3 ml of acetonitril was added 2-phenyl-3-methylbutylamine hydrochloride (0.147 g, 0.738 mmol, 1 eq.) at room temperature followed by triethylamine (TEA) (0.164 g, 1.62 mmol, 2.2 eq.). The reaction was microwaved (130° C., 600 s, fixed hold, high absorption) and the solvent evaporated. The residual oil was subjected to column chromatography to give ethyl (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-3-[(3-methyl-2-phenylbutyl)amino]acrylate (0.253 g, 85% yield) as a mixture of 2 atropoisomers.

¹H-NMR (400 MHz, DMSO-d₆/DMSO-d₅=2.50, water signal=3.33): 9.73 (m, 1H for isomer 1), 9.65 (m, 1H for isomer 2), 8.63 (m, 1H for isomerl and 1H for isomer 2), 7.96 (m, 1H for isomer 1), 7.66-7.53 (m, 1H for isomer 1 and 2H for isomer 2), 7.37-7.25 (m, 3H for isomer 1 and 3H for isomer 2), 7.19 (m, 1H for isomer 1 and 1H for isomer 2), 7.13 (m, 1H for isomer 1 and 1H for isomer 2), 4.13 (2H for isomer 1 and 2H for isomer 2), 3.50 (m, 2H for isomer 1), 3.34 (bs, 1H for isomer 1 and 1H for isomer 2), 3.25 (m, 2H for isomer 2), 2.55 (m, 1H for isomer 1), 2.45 (m, 1H for isomer 2), 1.79 (m, 1H for isomer 1 and 1H for isomer 2), 1.18-0.5 (m, 9H for isomer 1 and 9H for isomer 2).

LogP: 4.21

To a solution of ethyl 3-chloro-3-(2-chloropyridin-3-yl)-2-cyanoacrylate (0.1 g, 0.369 mmol, 1 eq.) in 5 ml of tetrahydrofuran were added 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanamine hydrochloride (0.106 g, 0.40 mmol, 1.1 eq.) and triethylamine (TEA) (0.112 g, 1.10 mmol, 3 eq.) at room temperature. After being stirred for 8 h at 80° C., the mixture was evaporated. The residue was diluted with AcOEt and the precipitate was filtered off. The filtrate was evaporated and the residual oil was subjected to column chromatography to give ethyl (2Z)-3-(2-chloropyridin-3-yl)-3-({2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}amino)-2-cyanoacrylate (0.170 g, 99% yield).

¹H-NMR (400 MHz, CDCl₃/CDCl₃=7.26): 10.46 (bs, 1H), 8.76 (S, 1H), 8.57-8.60 (m, 1H), 7.92 (s, 1H), 7.68 (dd, 1H), 7.44 (dt, 1H), 4.26 (q, 2H), 3.50-3.69 (m, 2H), 3.18-3.28 (m, 2H), 1.33 (t, 3H).

LogP: 3.57

To a solution of ethyl 3-chlor-3-(2-chloropyridin-3-yl)-2-cyanoacrylate (0.150 g, 0.55 mmol, 1 eq.) in 3 ml of acetonitrile was added 1-(6-chloropyridin-3-yl)ethanamine (0.103 g, 0.66 mmol, 1.2 eq.) followed by triethylamine (TEA) (0.167 g, 1.66 mmol, 3 eq.). The reaction was microwaved (130° C., 600 s, fixed hold, high absorption) and the solvent evaporated. The residual oil was subjected to column chromatography to give ethyl (2Z)-3-(2-chloropyridin-3-yl)-3-{[1-(6-chloropyridin-3-yl)ethyl]amino}-2-cyanoacrylate (0.157 g, 68% yield) as a mixture of 2 atropoisomers.

¹H-NMR (250 MHz, CDCl₃/CDCl₃=7.26): 10.32-10.29 (bm, 1H for isomer 1 and 1H for isomer 2), 8.58 (dd, 1H for isomer 1, J=1.9 and 4.8 Hz), 8.53 (dd, 1H for isomer 2, J=2.3 and 4.8 Hz), 8.15 (d, J=2.5 Hz, 1H for isomer 1), 7.85 (d, 1H for isomer 2, J=2.3 Hz), 7.9 (dd, 1H for isomer 1, J=2.0 and 7.7 Hz), 7.56-7.19 (m, 4H for isomer 1 and 4H for isomer 2), 4.36-4.27 (m, 3H for isomer 1 and 3H for isomer 2), 1.64 (d, 3H for isomer 2, J=6.7 Hz), 1.52 (td, 3H for isomer 1, J=7.0 Hz), 1.981-1.41 (m, 3H for isomer 1 and 3H for isomer 2)

LogP: 2.80

To a solution of ethyl 3-chloro-3-(3-chloro-4-methyl-2-thienyl)-2-cyanoacrylate (0.351 g, 1.21 mmol, 1 eq.) in 3 ml of acetonitrile was added N-methyl-L-alaninamide hydrochloride (0.201 g, 1.45 mmol, 1.2 eq.) followed by triethylamine (TEA) (0.490 g, 4.84 mmol, 4 eq.). The reaction was microwaved (130° C., 300 s, fixed hold, high absorption) and the solvent evaporated. The residual oil was triturated in ethyl acetate and the white solid removed by filtration. After concentration under vacuum, the residual oil was subjected to column chromatography to give ethyl (2Z)-3-(3-chloro-4-methyl-2-thienyl)-2-cyano-3-{[(2R)-1-(methylamino)-1-oxopropan-2-yl]amino}acrylate (0.26 g, 57% yield) as a mixture of atropoisomers.

¹H-NMR (400 MHz, DMSO-d₆/DMSO-d₅=2.50, water signal=3.33): 10.25 (m, 1H), 8.05 (m, 1H) 7.75 (m, 1H), 4.2 (m, 2H), 3.93 (m, 1H), 2.60 (m, 3H), 2.20 (m, 3H), 1.26 (m, 6H).

LogP: 3.61

Example of Process P2

Allyl (2Z)-3-(3-bromo-2-thienyl)-2-cyano-3-{[1-(1,3-thiazol-2-yl)ethyl]amino}acrylate (0.1 g, 0.212 mmol, 1 eq.) was dissolved in 5 ml of DCM under Argon and cooled to 0° C. Pyrrolidine (0.018 g, 0.255 mmol, 1.2 eq.) added followed by triphenylphosphine (0.010 g, 0.038 mmol, 0.18 eq.) and tetrakis(triphenylphosphine)palladium(0) (0.012 g, 0.011 mmol, 0.05 eq.). The reaction was stirred at 0° C. for 2 h at which point no starting material remained. The reaction medium was quenched with aqueous HCl 1N (5 ml) and diluted with water. The organic layer was basified with aqueous 1N NaOH until pH 9 and was extracted again with aqueous 1N NaOH. The aqueous layers were combined, acidified with aqueous 1N HCl and extracted with DCM (CH₂Cl₂). The organic layers were combined, dried over MgSO₄ and concentrated under vacuum to give (2Z)-3-(3-bromo-2-thienyl)-2-cyano-3-{[1-(1,3-thiazol-2-yl)ethyl]amino}acrylic acid (0.075 g, 87% yield) as a white solid and a mixture of atropoisomers.

¹H-NMR (250 MHz, DMSO-d₆/DMSO-d₅=2.50, water signal=3.33): 13.14 (bs, 1H), 10.57 (d, 1H for isomer 1, J=8.6 Hz), 10.45 (d, 1H for isomer 2, J=8.9 Hz), 8.04 (d, in for isomer 1, J=5.1 Hz), 7.94 (d, 1H for isomer 2, J=5.4 Hz), 7.80 (m, 1H for isomer 1 and 1H for isomer 2), 7.73 (m, 1H for isomer 1 and 1H for isomer 2), 7.32 (d, 1H for isomer 2, J=5.4 Hz), 7.29 (d, 1H for isomer 1, J=5.1 Hz), 4.79 (m, 1H for isomer 1 and 1H for isomer 2), 1.65 (d, 3H for isomer 2, J=7.0 Hz), 1.57 (d, 3H for isomer 1, J=6.7 Hz).

LogP: 1.23

To a solution of (2Z)-3-(3-bromo-2-thienyl)-2-cyano-3-{[1-(1,3-thiazol-2-yl)ethyl]amino}acrylic acid (0.18 g, 0.468 mmol, 1 eq.) in 5 ml of DCM (CH₂Cl₂) were added isopropylamine (0.083 g, 1.40 mmol, 3 eq.), hydroxybenzotriazole (HOBT) (0.066 g, 0.49 mmol, 1.05 eq.) and diisopropylethylamine (DIPEA) (0.090 g, 0.70 mmol, 1.5 eq.). The reaction was cooled to 0° C. and dicyclohexylcarbodiimide (DCC) (0.101 g, 0.49 mmol, 1.05 eq.) was added. Stirring was allowed overnight and the solid formed removed by filtration. The solvent was removed under reduced pressure and the residual oil submitted to chromatography on silica gel to give 2Z)-3-(3-bromo-2-thienyl)-2-cyano-N-isopropyl-3-{[1-(1,3-thiazol-2-yl)ethyl]amino}acrylamide (0.090 g, 43% yield) as a white solid and a mixture of atropoisomers.

¹H-NMR (250 MHz, DMSO-d₆/DMSO-d₅=2.50, water signal=3.33): 11.36 (d, 1H of isomer 1, J=9.2 Hz), 11.30 (d, 1H of isomer 2, J=9.8 Hz), 8.01 (d, 1H of isomer 1, J=5.6 Hz), 7.91 (d, 1H of isomer 2, J=5.1 Hz), 7.79 (m, 1H for isomer 1 and 1H for isomer 2), 7.71 (m, 1H for isomer 1 and 1H for isomer 2), 7.29 (m, 2H of isomer 1 and 2H of isomer 2), 4.69 (m, 1H of isomer 1 and 11-1 of isomer 2), 4.01 (m, 1H of isomer 1 and 1H of isomer 2), 1.64 (d, 3H for isomer 2, J=7.0 Hz), 1.54 (d, 3H for isomer 1, J=6.6 Hz), 1.14 (m, 6H of isomer 1 and 6H of isomer 2).

LogP: 3.11

Example of Process P3

A solution of ethyl (2Z)-2-cyano-3-[3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl]-3-{[1-(1,3-thiazol-2-yl)ethyl]amino}acrylate (0.122 g, 0.32 mmol, 1 eq.) in 3 ml of toluene was treated with ethylamine (1 M solution in tetrahydrofurane, 0.96 ml, 0.96 mmol, 3 eq.) and AlMe₃ (1 M solution in toluene, 0.96 ml, 0.96 mmol, 3 eq.). The reaction was microwaved at 110° C. for 1800s (fixed hold, high absorption). The reaction was quenched with aqueous saturated NH₄Cl and extracted with ethylacetate. The organic layers were combined and dried over MgSO₄ and concentrated under vacuum. The residue was purified by chromatography on silica gel to give (2Z)-2-cyano-N-cyclopropyl-3-[3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl]-3-{[1-(1,3-thiazol-2-yl)ethyl]amino}acrylamide (0.068 g, 51% yield) as a mixture of atropoisomers.

¹H-NMR (250 MHz, CDCl₃/CDCl₃=7.26): 11.40 (d, 1H for isomer 1, J=9.5 Hz), 11.22 (d, 1H for isomer 2, J=9.5 Hz), 7.73 (m, 1H for isomer 1 and 1H for isomer 2), 7.60 (s, 1H for isomer 1), 7.38 (s, 1H for isomer 2), 7.30 (m, 1H for isomer 1 and 1H for isomer 2), 6.78 (t, 1H for isomer 2, J=54.7 Hz), 6.67 (t, 1H for isomer 1, J=54.7 Hz), 6.11 (bs, 1H for isomer 1 and 1H for isomer 2), 4.77 (m, 1H for isomer 1 and 1H for isomer 2), 4.02 (s, 3H for isomer 1), 3.91 (s, 3H for isomer 2), 2.73 (m, 1H for isomer 1 and 1H for isomer 2), 1.70 (d, 3H for isomer 2, J=7 Hz), 1.61 (d, 3H for isomer 1, J=7 Hz), 0.83 (m, 2H for isomer 1 and 2H for isomer 2), 0.59 (m, 2H for isomer 1 and 2H for isomer 2).

LogP: 2.04

Example of Process P4

A mixture of ethyl (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-3-(ethylamino)acrylate (0.284 g, 1.01 mmol, 1 eq.) 4-chloro-pjhenylboronic acid (0.207 g, 1.32 mmol, 1.3 eq.) and K₂CO₃ (in 1 ml of water, 0.281 g, 2.02 mmol, 2 eq.) in 20 ml of dimethyl ether (DME) and 0.6 ml of ethanol was degassed with argon. Tetrakis(triphenylphosphine)palladium(0) (0.117 g, 0.1 mmol, 0.1 eq.) was added to the mixture under argon atmosphere and the mixture was heated under reflux for 6 h. The reaction mixture was cooled, extracted with AcOEt. After drying over MgSO₄, the solution was concentrated in vacuo to obtain crude product, which was purified by column chromatography to give ethyl (2Z)-3-[2-(4-chlorophenyl)pyridin-3-yl]-2-cyano-3-(ethylamino)acrylate (0.24 g, 66% yield).

¹H-NMR (400 MHz, CDCl₃/CDCl₃=7.26): 9.76 (bs, 1H), 8.84 (dd, 1H), 7.75 (dd, 1H), 7.63-7.66 (dd, 1H), 7.40-7.46 (m, 4H), 4.23-4.31 (m, 2H), 2.76-2.87 (m, 2H), 1.36 (t, 3H), 1.24 (t, 3H).

LogP: 2.96

Example of Process P6

A solution of 3-(2-chloropyridin-3-yl)-3-[(2-ethylcyclopropyl)amino]acrylonitrile (0.15 g, 0.606 mmol, 1 eq.) in 2 ml of dimethyl formamide (DMF) was treated with NaH (60% in mineral oil, 0.029 g, 0.727 mmol, 1.2 eq.) and stirring allowed for 1 h. ethylisothiocyanate (0.105 g, 1.21 mmol, 2 eq.) was added and stirring continued overnight. The reaction was quenched with water and extracted with AcOEt. The organic layers were combined, dried over MgSO₄ and concentrated under vacuum. The residue was purified by chromatography on silica gel to give (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-N-ethyl-3-[(2-ethylcyclopropyl)amino]-prop-2-enethioamide (0.059 g, 27% yield) as a white solid.

¹H-NMR (500 MHz, DMSO-d₆/DMSO-d₅=2.50, water signal=3.33): 12.77 (bd, 1H, J=3.1 Hz), 8.96 (m, 1H), 8.68 (m, 1H), 8.26 (m, 1H), 7.73 (m, 1H), 3.65 (m, 2H), 2.31 (m, 1H), 1.18 (t, 3H, J=7.2 Hz), 1.05-0.83 (m, 5H), 0.62 (dd, 2H, J=6.3 and 13.5 Hz), 0.56 (m, 1H).

LogP: 3.87

Example of Process P8

To a solution of ethyl 3-(3-chloro-4-methyl-2-thienyl)-2-cyano-3-oxopropanoate (15.40 g, 56.67 mmol, 1 eq.) in 200 ml of CHCl₃ was added POCl₃ (86.9 g, 566 mmol, 10 eq.). Et₃N (14.33 g, 141.6 mmol, 2.5 eq.) was added dropwise with stirring at 5° C., and the mixture was refluxed for 4 h. The mixture was evaporated. After evaporation, the mixture was diluted with DCM (CH₂Cl₂) and with ice water and was extracted with DCM (CH₂Cl₂) and washed with brine. The organic layers were combined and dried over MgSO₄ before concentration under reduced pressure. The residue was subjected to column chromatography on silica gel to give ethyl 3-chloro-3-(3-chloro-4-methyl-2-thienyl)-2-cyanoacrylate (11 g, 66% yield) as a mixture of 2 isomers

¹H-NMR (400 MHz, DMSO-d₆/DMSO-d₅=2.50, water signal=3.33): 8.13 (s, 1H for isomer 1), 7.91 (s, 1H for isomer 2), 4.42 (q, 2H for isomer 1, J=7 Hz), 4.152 (q, 2H for isomer 2, J=7.1 Hz), 2.24 (s, 3H for isomer 1), 2.18 (s, 3H for isomer 2), 1.30 (t, 3H for isomer 1, J=7 Hz), 1.10 (t, 3H for isomer 2, J=7.1 Hz).

LogP: 3.65, 3.70

Example of Process P9

To a solution of 3-chloro-3-(2-chloropyridin-3-yl)acrylonitrile (1.4 g, 7.03 mmol, 1 eq.) in 15 ml of acetonitrile was added 2-ethylcyclopropanamine hydrochloride (1.02 g, 8.44 mmol, 1.2 eq.) followed by triethylamine (TEA) (1.06 g, 10.55 mmol, 1.5 eq.). The reaction was microwaved (130° C., 2000 s, fixed hold, high absorption) and the solvent evaporated. The residual oil was triturated in ethyl acetate and the white solid removed by filtration. After concentration under vacuum, the residual oil was subjected to column chromatography to give 3-(2-chloropyridin-3-yl)-3-[(2-ethylcyclopropyl)amino]acrylonitrile (0.998 g, 51% yield).

¹H-NMR (400 MHz, DMSO-d₆/DMSO-d₅=2.50, water signal=3.33): 8.50 (m, 1H), 7.87 (bd, 1H, J=7.9 Hz), 7.53 (m, 1H), 4.43 (s, 1H), 2.20 (bs, 1H), 1.44 (bs, 1H), 1.20 (m, 1H), 0.95 (m, 4H), 0.67 (bs, 1H), 0.59 (m, 1H).

LogP: 2.53

Example of Process P10

100 ml of dimethyl formamide (DMF) were cooled to 0° C. and POCl₃ (35.47 g, 231 mmol, 3 eq.) added dropwise. The reaction was stirred 30 min at 0° C. and a solution of 2-chloro-3-acetyl-pyridine (12 g, 77.12 mmol, 1 eq.) in 15 ml of dimethyl formamide (DMF) was added. Once all added the reaction was warmed to 50° C. and stirred for 8 h. The mixture was cooled to 0° C. and hydroxylamine hydrochloride (21.43 g, 308 mmol, 4 eq.) was added by portions very carefully (exothermic). Once all added the reaction was stirred at room temperature for 2 h and quenched with water. The medium was basified until pH 2-3 was reached with 1N aqueous NaOH and extracted with ethylacetate. The organic layer was washed with brine and dried over MgSO₄. Removal of all volatiles under reduced pressure afforded 3-chloro-3-(2-chloropyridin-3-yl)acrylonitrile (13.21 g, 81% yield) as a mixture of isomers which was used without further purification.

LogP: 1.94, 2.03

In analogy to the examples above and according to the general description of the processes of preparing the compounds according to the invention the compounds in the following Table 1 may be obtained.

TABLE 1 (I)

No. R¹ Y² Y¹ Het R Log P M⁺ 1 Et O O 3,6-dichloropyridin-2-yl (1R)-1-(1-naphthyl)ethyl 4.4^([a]) 2 Et O O 3,5-dichloropyridin-2-yl (1S)-1-(1-naphthyl)ethyl 4.65^([a]) 440 3 Et O O 4,6-dichloropyridin-3-yl (1S)-1-(1-naphthyl)ethyl 4.4^([a]) 4 Me O O 6-chloropyridin-2-yl 1-(1,3-thiazol-2-yl)ethyl 5 Me O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 6 Et O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.58^([a]); 2.5^([c]) I2; 2.5^([c]) T1; 2.65^([c]) T2; 363 2.34^([c]) I1; 2.4^([b]); 2.41 ^([b]) I2; 2.41^([b]) I1 7 Et O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)propyl 2.79^([c]) T2; 2.61^([c]) T1; 2.71^([b]) T1; 2.71^([b]) T2 8 Me O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)propyl 2.29^([c]) T1; 2.46^([c]) T2; 2.39^([b]) T2; 2.39^([b]) T1 9 Me O O 2-chloropyridin-3-yl 2-methyl-1-(1,3-thiazol-2- 2.56^([c]) T1; 2.73^([c]) T2; 2.66^([b]) T1; yl)propyl 2.72^([b]) T2 10 nBu O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 3.04^([c]) T1; 3.23^([c]) T2; 3.15^([b]) T1; 3.15^([b]) T2 11 Me O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)butyl 2.82^([c)] T2; 2.64^([c]) T1; 2.75^([b]) T1; 2.75^([b]) T2 12 2-EtOEt O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.46^([c]) T2; 2.32^([c]) T1; 2.4^([b]) T1; 2.4^([b]) T2 13 Me O O 2-chloropyridin-3-yl pyrimidin-2-ylmethyl 1.57^([c]); 1.57^([b]) 14 Me O O 2-chloropyridin-3-yl 1,3-dioxolan-2-ylmethyl 1.79^([c]); 1.77^([b]) 15 Me O O 2-chloropyridin-3-yl 1-(1,3-benzothiazol-2-yl)ethyl 2.88^([c]) T1; 3.03^([c]) T2; 2.95^([b]) 16 Me O O 2-chloropyridin-3-yl tetrahydrofuran-2-ylmethyl 2.06^([c]) I2; 2.03^([c]) I1; 2.03^([b]) 17 Me O O 2-methyl-4-trifluoromethyl- 1-(1,3-thiazol-2-yl)ethyl 2.78^([a]); 2.66^([c]); 2.63^([b]) 403 1,3-thiazol-5-yl 18 Me O O 3-chlorothiophen-2-yl 1-(1,3-thiazol-2-yl)ethyl 2.61^([c]); 2.59^([b]) 19 Me O O 2-chloropyridin-3-yl 1-(4,5-dimethyl-1,3-thiazol- 2.74^([c]) T1; 2.91^([c]) T2; 2.69^([b]) 2-yl)ethyl 20 Me O O 2-chloropyridin-3-yl tetrahydrothiophen-2-ylmethyl 2.63^([c]); 2.47^([b]) 21 Me O O 2-bromopyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.36^([c]) T2; 2.2^([c]) T1; 2.12^([b]) 22 Me O O 2-chloropyridin-3-yl tetrahydrothiophen-3-yl 2.4^([c]); 2.23^([b]) 23 iPr O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.96^([c]) T2; 2.78^([c]) T1; 2.7^([b]) 24 Et O O 2-chloro-6-methylpyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.71^([c]) T1; 2.87^([c]) T2; 2.62^([b]) 25 tBu O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 3.3^([c]) T2; 3.1^([c]) T1; 3.07^([b]) 26 Me O O 2-chloropyridin-3-yl 1-(2,4-dimethyl-1,3-thiazol- 2.11^([c]) T1; 2.37^([c]) T2; 2.17^([b]) 5-yl)ethyl 27 Me O O 3-chloro-4-methylthiophen-2-yl 1-(1,3-thiazol-2-yl)ethyl 3.03^([c]); 2.91^([b]) 28 iBu O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 3.16^([c]) T1; 3.36^([c]) T2; 3.13^([b]) 29 iPr O O 2-chloropyridin-3-yl 1-(1,3-benzothiazol-2-yl)ethyl 3.68^([c]) T1; 3.89^([c]) T2; 3.63^([b]) 30 CH₂CF₃ O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.9^([c]) T2; 2.77^([c]) T1; 2.67^([b]) 31 Et O O 2,5-dichloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.98^([c]) T1; 3.15^([c]) T2; 2.95^([b]) 32 Et O O 3-(difluoromethyl)-1-methyl- pyridin-2-ylmethyl 1.94^([a]) 362 1H-pyrazol-4-yl 33 Et O O 3-(difluoromethyl)-1-methyl 1-(4,5-dimethyl-1,3-thiazol-2- 2.96^([a]) 410 1H-pyrazol-4-yl yl)ethyl 34 Et O O 3-(difluoromethyl)-1-methyl- 1-(1,3-thiazol-2-yl)ethyl 2.4^([a]) 382 1H-pyrazol-4-yl 35 Et O O 3-(difluoromethyl)-1-methyl- 1-(1H-indol-3-yl)propan-2-yl 3.25^([a]) 428 1H-pyrazol-4-yl 36 Et O O 3-(difluoromethyl)-1-methyl- 1-(pyridin-2-yl)ethyl 2.33^([a]) 376 1H-pyrazol-4-yl 37 Et O O 3-chloro-5-(trifluoro- 1-(4,5-dimethyl-1,3-thiazol-2- 4.04^([a]) 459 methyl)pyridin-2-yl yl)ethyl 38 Et O O 5-fluoro-1,3-dimethyl-1H- 1-(1,3-thiazol-2-yl)ethyl 2.37^([a]) 364 pyrazol-4-yl 39 Et O O 5-fluoro-1,3-dimethyl-1H- pyridin-2-ylmethyl 1.91^([a]) 344 pyrazol-4-yl 40 Et O O 3-chloro-5-(trifluoro- 1-(1,3-thiazol-2-yl)ethyl 3.37^([a]) 431 methyl)pyridin-2-yl 41 Et O O 3-chloro-5-(trifluoro- 1-(1H-indol-3-yl)propan-2-yl 4.07^([a]) 477 methyl)pyridin-2-yl 42 Et O O 3-chloro-5-(trifluoro- pyridin-2-ylmethyl 2.98^([a]) 411 methyl)pyridin-2-yl 43 Et O O 3-chloro-5-(trifluoro- 1-(pyridin-2-yl)ethyl 3.44^([a]) 425 methyl)pyridin-2-yl 44 Et O O 2-chloropyridin-3-yl 2-oxotetrahydrothiophen-3-yl 2.42^([c]); 2.23^([b]) 45 Et O O 5-fluoro-1,3-dimethyl-1H- 1-(4,5-dimethyl-1,3-thiazol-2- 2.94^([a]) 392 pyrazol-4-yl yl)ethyl 46 Et O O 5-fluoro-1,3-dimethyl-1H- 1-(1H-indol-3-yl)propan-2-yl 3.07^([a]) 410 pyrazol-4-yl 47 Me O O 3-(difluoromethyl)-1-methyl- 1-(4,5-dimethyl-1,3-thiazol-2- 2.65^([a]) 396 1H-pyrazol-4-yl yl)ethyl 48 Et O O 3-(difluoromethyl)-1-methyl- 1-(1-benzothiophen-2-yl)-2,2,2- 4.1^([a]) 485 1H-pyrazol-4-yl trifluoroethyl 49 Et O O 2-chloropyridin-3-yl 1-[3-chloro-5- 4^([c]) I2; 3.9^([c]) I1; 3.76^([b]) (trifluoromethyl)pyridin-2- yl]propan-2-yl 50 Et O O 5-fluoro-1,3-dimethyl-1H- 1-(pyridin-2-yl)ethyl 2.28^([a]) 358 pyrazol-4-yl 51 Et O O 5-fluoro-1,3-dimethyl-1H- 1-(1-benzothiophen-2-yl)-2,2,2- 4.25^([a]) 467 pyrazol-4-yl trifluoroethyl 52 Et O O 2,5-dimethylfuran-3-yl 1-(1,3-thiazol-2-yl)ethyl 53 Et O O 4,5-dichloro-1,2-thiazol-3-yl 1-(4,5-dimethyl-1,3-thiazol-2- 4.01^([a]) 431 yl)ethyl 54 Et O O 4,5-dichloro-1,2-thiazol-3-yl 1-(1H-indol-3-yl)propan-2-yl 4.1^([a]) 449 55 Et O O 4,5-dichloro-1,2-thiazol-3-yl 1-(1,3-thiazol-2-yl)ethyl 3.29^([a]) 4.03 56 F₃iPr O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 3.2^([c]) I2; 3.09^([c]) I1; 2.94^([b]) 57 Me O O 3-(difluoromethyl)-1-methyl- 1-(1H-indol-3-yl)propan-2-yl 3^([a]) 414 1H-pyrazol-4-yl 58 Me O O 3-(difluoromethyl)-1-methyl- pyridin-2-ylmethyl 1.63^([a]) 348 1H-pyrazol-4-yl 59 Me O O 3-(difluoromethyl)-1-methyl- 1-(pyridin-2-yl)ethyl 2.05^([a]) 362 1H-pyrazol-4-yl 60 Me O O 3-(difluoromethyl)-1-methyl- 1-(1-benzothiophen-2-yl)-2,2,2- 3.83^([a]) 471 1H-pyrazol-4-yl trifluoroethyl 61 Me O O 3-(difluoromethyl)-1-methyl- 1-(1,3-thiazol-2-yl)ethyl 2.13^([a]) 368 1H-pyrazol-4-yl 62 Et O O 2-(methylsulfanyl)pyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.75^([c]) T1; 2.94^([c]) T2; 2.73^([b]) 63 Et O O 1-methyl-3-(trifluoromethyl)- 1-(1,3-thiazol-2-yl)ethyl 2.78^([a]) 400 1H-pyrazol-4-yl 64 Et O O 1-methyl-3-(trifluoromethyl)- 1-(4,5-dimethyl-1,3-thiazol-2- 3.48^([a]) 428 1H-pyrazol-4-yl yl)ethyl 65 Et O O 1-methyl-3-(trifluoromethyl)- 1-(1H-indol-3-yl)propan-2-yl 3.73^([a]) 446 1H-pyrazol-4-yl 66 Et O O 2-chloropyridin-3-yl 1,3-thiazol-2-ylmethyl 2.07^([a]) 348 67 Me O O 3-(difluoromethyl)-1-methyl- 1,3-thiazol-2-ylmethyl 1.72^([a]) 354 1H-pyrazol-4-yl 68 Et O O 3-(difluoromethyl)-1-methyl- 1.3-thiazol-2-ylmethyl 2^([a]) 368 1H-pyrazol-4-yl 69 Et O O 4,5-dichloro-1,2-thiazol-3-yl 1-(1-benzothiophen-2-yl)-2,2,2- 5.11^([a]) 505 trifluoroethyl 70 Et O O 4,5-dichloro-1,2-thiazol-3-yl pyridin-2-ylmethyl 2.84^([a]) 383 71 Et O O 4,5-dichloro-1,2-thiazol-3-yl 1-(pyridin-2-yl)ethyl 3.35^([a]) 397 72 Et O O 2,6-dichloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 3.05^([c]) T1; 3.24^([c]) T2; 3.01^([b]) 73 Et O O 3-chloro-5-(trifluoro- 1-(1-benzothiophen-2-yl)-2,2,2- 4.94^([a]) 534 methyl)pyridin-2-yl trifluoroethyl 74 Et O O 3-methylisoxazol-4-yl 1-(4,5-dimethyl-1,3-thiazol-2- 3.02^([a]) 361 yl)ethyl 75 Et O O 3-chloro-5-(trifluoro- 1,3-thiazol-2-ylmethyl 2.84^([a]) 417 methyl)pyridin-2-yl 76 Et O O 3-methylisoxazol-4-yl 1,3-thiazol-2-ylmethyl 2.04^([a]) 319 77 Et O O 3-methylisoxazol-4-yl 1-(1,3-thiazol-2-yl)ethyl 2.4^([a]) 333 78 Et O O 3-methylisoxazol-4-yl 1-(1H-indol-3-yl)propan-2-yl 3.15^([a]) 379 79 Et O O 2-fluoropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.47^([c]); 2.32^([b]) 80 Et O O 5-fluoro-1,3-dimethyl-1H- 1,3-thiazol-2-ylmethyl 2.01^([a]) 350 pyrazol-4-yl 81 Et O O 3-methylisoxazol-4-yl pyridin-2-ylmethyl 1.96^([a]) 313 82 Et O O 3-methylisoxazol-4-yl 1-(pyridin-2-yl)ethyl 2.36^([a]) 327 83 Me O O 3-chloro-5-(trifluoro- 1,3-thiazol-2-ylmethyl 2.63^([a]) 403 methyl)pyridin-2-yl 84 Et O O 2-chloropyridin-3-yl (2S)-1-(1H-1,2,4-triazol-1- 1.79^([c]) I2; 1.87^([c]); 1.67^([c]) I1; 1.59^([b]) yl)propan-2-yl 85 Et O O 3-bromothiophen-2-yl 1-(1,3-thiazol-2-yl)ethyl 3.13^([a]) 412 86 Et O O 5-chloro-1,3-dimethyl-1H- 1,3-thiazol-2-ylmethyl 2.13^([a]) 366 pyrazol-4-yl 87 Et O O 5-chloro-1,3-dimethyl-1H- pyridin-2-ylmethyl 2.02^([a]) 360 pyrazol-4-yl 88 Et O O 3-bromothiophen-2-yl 1,3-thiazol-2-ylmethyl 2.67^([a]) 398 89 allyl O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.64^([c]) T1; 2.78^([c]) T2; 2.56^([b]) 90 H O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 91 Et O O 3-bromothiophen-2-yl 1-(1H-indol-3-yl)propan-2-yl 3.8^([a]) 458 92 Et O O 3-bromothiophen-2-yl 1-(4,5-dimethyl-1,3-thiazol-2- 3.8^([a]) 440 yl)ethyl 93 Et O O 3-methylisoxazol-4-yl 1-(1-benzothiophen-2-yl)-2,2,2- 4.24^([a]) 436 trifluoroethyl 94 Et O O 5-chloro-1,3-dimethyl-1H- 1-(4,5-dimethyl-1,3-thiazol-2- 3.12^([a]) 408 pyrazol-4-yl yl)ethyl 95 Et O O 3-(trifluoromethyl)thiophen- 1,3-thiazol-2-ylmethyl 2.82^([a]) 388 2-yl 96 Et O O 3-(trifluoromethyl)thiophen- 1-(1,3-thiazol-2-yl)ethyl 3.31^([a]) 402 2-yl 97 Et O O 3-(trifluoromethyl)thiophen- 1-(4,5-dimethyl-1,3-thiazol-2- 3.92^([a]) 430 2-yl yl)ethyl 98 Et O O 5-chloro-1,3-dimethyl-1H- 1-(1,3-thiazol-2-yl)ethyl 2.52^([a]) 380 pyrazol-4-yl 99 Et O O 3-bromothiophen-2-yl pyridin-2-ylmethyl 2.61^([a]) 392 100 Et O O 3-bromothiophen-2-yl 1-(pyridin-2-yl)ethyl 3.1^([a]) 406 101 iPr NH O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 102 Et O O 3-(trifluoromethyl)thiophen- pyridin-2-ylmethyl 2.84^([a]) 2-yl 103 Et O O 3-(trifluoromethyl)thiophen- 1-(pyridin-2-yl)ethyl 3.27^([a]) 396 2-yl 104 Et O O 2-bromothiophen-3-yl 1,3-thiazol-2-ylmethyl 2.66^([a]) 398 105 Et O O 2-bromothiophen-3-yl 1-(1,3-thiazol-2-yl)ethyl 3.1^([a]) 412 106 Et O O 2-bromothiophen-3-yl 1-(1H-indol-3-yl)propan-2-yl 3.8^([a]) 458 107 Et O O 3-(trifluoromethyl)thiophen- 1-(1-benzothiophen-2-yl)-2,2,2- 4.89^([a]) 505 2-yl trifluoroethyl 108 Et O O 3-(trifluoromethyl)thiophen- 1-(1H-indol-3-yl)propan-2-yl 3.94^([a]) 448 2-yl 109 Me O O 2-chloropyridin-3-yl 1-(pyridin-3-yl)ethyl 0.82^([a]) 110 Me O O 2-chloropyridin-3-yl 1-(pyridin-2-yl)ethyl 1.99^([a]) 111 Et O O 2-chloropyridin-3-yl (2R)-1-[3,5-bis(trifluoromethyl)- 1H-pyrazol-1-yl]propan-2-yl 112 Et O O 2-bromothiophen-3-yl 1-(4,5-dimethyl-1,3-thiazol-2- 3.7^([a]) 440 yl)ethyl 113 Et O O 5-chloro-1,3-dimethyl-1H- 1-(1H-indol-2-yl)propan-2-yl 3.24^([a]) 426 pyrazol-4-yl 114 Et O O 2-chloropyridin-3-yl (2S)-1-[3,5-bis(trifluoromethyl)- 1H-pyrazol-1-yl]propan-2-yl 115 Et O O 2-bromothiophen-3-yl pyridin-2-ylmethyl 2.53^([a]) 392 116 Et O O 2-bromothiophen-3-yl 1-(pyridin-2-yl)ethyl 3.1^([a]) 406 117 Et O O 2-chloropyridin-3-yl 2-(methylsulfanyl)pyridin-3-yl 118 Et O O 2,5-dimethylfuran-3-yl 1-(tetrahydrofuran-2-yl)ethyl 3.27^([a]) 119 Et O O 2,5-dimethylfuran-3-yl 2-oxoazepan-3-yl 2.14^([a]) 120 Me O O 2-chloropyridin-3-yl oxetan-3-yl 1.35^([a]) 121 Me O O 2-chloropyridin-3-yl 1-cyclopropyl-2-(morpholin-4- 1.38^([a]) yl)ethyl 122 Me O O 2-chloropyridin-3-yl thietan-3-yl 2.08^([a]) 123 Me O O 2-chloropyridin-3-yl 2-oxoazepan-3-yl 1.57^([a]) 124 Me O O 2-chloropyridin-3-yl 1-(5-bromo-3-chloropyridin-2- 3.24^([a]) yl)ethyl 125 Me O O 2-chloropyridin-3-yl 1,1-dioxidotetrahydrothiophen-3-yl 1.33^([a]) 126 Me O O 2-chloropyridin-3-yl 1-(tetrahydrofuran-2-yl)ethyl 2.17^([a]) 127 Et O O 2-chloropyridin-3-yl (2S)-1-[5-(methylsulfanyl)-3- 3.55^([c]) T1; 3.81^([c]) T2; 3.66^([b]) (pentafluoroethyl)-1H-1,2,4- triazol-1-yl]propan-2-yl 128 Et O O 2-chloropyridin-3-yl 1-(5-bromo-1,3-thiazol-2- 3.28^([c]) T1; 3.41^([c]) T2; 3.32^([b]) yl)ethyl 129 Et O O 3-bromothiophen-2-yl 1-(1-benzothiophen-2-yl)-2,2,2- 4.9^([a]) 515 trifluoroethyl 130 Et O O 2-bromothiophen-3-yl 1-(1-benzothiophen-2-yl)-2,2,2- 4.87^([a]) 515 trifluoroethyl 131 Me O O 2-methyl-4-trifluoromethyl- 1-(4,5-dimethyl-1,3-thiazol-2- 3.46^([a]) 431 1,3-thiazol-5-yl yl)ethyl 132 Me O O 2-methyl-4-trifluoromethyl- 1,3-thiazol-2-ylmethyl 2.33^([a]) 389 1,3-thiazol-5-yl 133 Me O O 2-methyl-4-trifluoromethyl- 1-(1H-indol-3-yl)propan-2-yl 3.6^([a]) 449 1,3-thiazol-5-yl 134 Me O O 2-methyl-4-trifluoromethyl- pyridin-2-ylmethyl 2.37^([a]) 383 1,3-thiazol-5-yl 135 Me O O 2-methyl-4-trifluoromethyl- 1-(pyridin-2-yl)ethyl 2.77^([a]) 397 1,3-thiazol-5-yl 136 Et O O 5-chloro-1,3-dimethyl-1H- 1-(pyridin-2-yl)ethyl 2.49^([a]) 374 pyrazol-4-yl 137 Et O O 5-chloro-1,3-dimethyl-1H- 1-(1-benzothiophen-2-yl)-2,2,2- 4.46^([a]) 483 pyrazol-4-yl trifluoroethyl 138 Et O O 1-methyl-3-(trifluoromethyl)- 1,3-thiazol-2-ylmethyl 2.43^([a]) 386 1H-pyrazol-4-yl 139 Et O O 1-methyl-3-(trifluoromethyl)- pyridin-2-ylmethyl 2.36^([a]) 380 1H-pyrazol-4-yl 140 Et O O 1-methyl-3-(trifluoromethyl)- 1-(pyridin-2-yl)ethyl 2.75^([a]) 394 1H-pyrazol-4-yl 141 Et O O 2-methyl-4-trifluoromethyl- 1,3-thiazol-2-ylmethyl 2.66^([a]) 403 1,3-thiazol-5-yl 142 Et O O 2-methyl-4-trifluoromethyl- 1-(1,3-thiazol-2-yl)ethyl 3.13^([a]) 417 1,3-thiazol-5-yl 143 Et O O 2-methyl-4-trifluoromethyl- 1-(4,5-dimethyl-1,3-thiazol-2- 3.83^([a]) 445 1,3-thiazol-5-yl yl)ethyl 144 Et O O 2-methyl-4-trifluoromethyl- pyridin-2-ylmethyl 2.7^([a]) 397 1,3-thiazol-5-yl 145 Et O O 2-methyl-4-trifluoromethyl- 1-(1H-indol-2-yl)propan-2-yl 3.85^([a]) 463 1,3-thiazol-5-yl 146 Et O O 2-methyl-4-trifluoromethyl- 1-(pyridin-2-yl)ethyl 3.12^([a]) 411 1,3-thiazol-5-yl 147 Et O O 1-methyl-3-(trifluoromethyl)- 1-(1-benzothiophen-2-yl)-2,2,2- 4.46^([a]) 503 1H-pyrazol-4-yl trifluoroethyl 148 Et O O 2-ethoxypyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.92^([c]); 2.89^([b]) 149 Et O O 3-chlorothiophen-2-yl 1-(1,3-thiazol-2-yl)ethyl 3.09^([a]) 368 150 Et O O 3-chlorothiophen-2-yl 1-(4,5-dimethyl-1,3-thiazol-2- 3.76^([a]) 396 yl)ethyl 151 Et O O 3-chlorothiophen-2-yl 1-(1H-indol-3-yl)propan-2-yl 3.8^([a]) 414 152 Et O O 2-methylpyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.28^([c]) T2; 2.12^([c]) T1; 2.17^([b]) 153 Et O O 3-chlorothiophen-2-yl 1,3-thiazol-2-ylmethyl 2.63^([a]) 354 154 Et O O 2-chloropyridin-3-yl (1S)-1-(1,3-thiazol-2-yl)ethyl] 155 Et O O 5-chloro-3-(difluoromethyl)- pyridin-2-ylmethyl 2.37^([a]) 396 1-methyl-1H-pyrazol-4-yl 156 Et O O 5-chloro-3-(difluoromethyl)- 1-(pyridin-2-yl)ethyl 2.81^([a]) 410 1-methyl-1H-pyrazol-4-yl 157 Et O O 2-iodothiophen-3-yl 1-(4,5-dimethyl-1,3-thiazol-2- 3.75^([a]) 488 yl)ethyl 158 Et O O 2-iodothiophen-3-yl 1-(1,3-thiazol-2-yl)ethyl 3.08^([a]) 460 159 Et O O 3-chlorothiophen-2-yl pyridin-2-ylmethyl 2.56^([a]) 348 160 Et O O 3-chlorothiophen-2-yl 1-(pyridin-2-yl)ethyl 3.05^([a]) 362 161 Et O O 2-iodothiophen-3-yl 1,3-thiazol-2-ylmethyl 2.68^([a]) 446 162 Et O O 3-chlorothiophen-2-yl 1-(1-benzothiophen-2-yl)-2,2,2- 4.89^([a]) 471 trifluoroethyl 163 Et O O 2-iodothiophen-3-yl 1-(pyridin-2-yl)ethyl 3.03^([a]) 454 164 Et O O 2-iodothiophen-3-yl 1-(1H-indol-3-yl)propan-2-yl 3.8^([a]) 506 165 Et O O 2-iodothiophen-3-yl 1-(1-benzothiophen-2-yl)-2,2,2- 4.81^([a]) trifluoroethyl 166 Et O O 2-iodothiophen-3-yl pyridin-2-ylmethyl 2.56^([a]) 440 167 Et O O 3-bromothiophen-2-yl 1-(4-methyl-1,3-thiazol-2- 3.44^([a]) yl)ethyl 168 Et O O 3-bromothiophen-2-yl 1-(4-methyl-1,3-thiazol-2- 2.92^([a]) 412 yl)ethyl 169 Et O O 3-bromothiophen-2-yl 1-(5-methyl-1,3-thiazol-2- 3.46^([a]) 426 yl)ethyl 170 Et O O 3-bromothiophen-2-yl 1,3-benzothiazol-2-ylmethyl 3.53^([a]) 448 171 Et O O 3-bromothiophen-2-yl 4-(trifluoromethyl)-1,3-thiazol- 3.37^([a]) 466 2-yl]methyl 172 Et O O 3-(trifluoromethyl)thiophen- 1-(tetrahydrofuran-2-yl)ethyl 3.55^([a]) 389 2-yl 173 Et O O 3-(trifluoromethyl)thiophen- 1-(2,4-dimethyl-1,3-thiazol-5- 2-yl yl)ethyl 174 Et O O 3-(trifluoromethyl)thiophen- 1-(4-methyl-1,3-thiazol-2- 3.58^([a]) 416 2-yl yl)ethyl 175 Et O O 3-(trifluoromethyl)thiophen- (4-methyl-1,3-thiazol-2- 3.11^([a]) 402 2-yl yl)methyl 176 Et O O 3-(trifluoromethyl)thiophen- 1,3-benzothiazol-2-ylmethyl 3.67^([a]) 438 2-yl 177 Et O O 3-(trifluoromethyl)thiophen- (4-trifluoromethyl-1,3-thiazol-2- 3.51^([a]) 456 2-yl yl)methyl 178 Me O O 2-methyl-4-trifluoromethyl- 1-(tetrahydrofuran-2-yl)ethyl 1.97^([a]) 390 1,3-thiazol-5-yl 179 Me O O 2-methyl-4-trifluoromethyl- 1-(2,4-dimethyl-1,3-thiazol-5- 2.8^([a]) 431 1,3-thiazol-5-yl yl)ethyl 180 Me O O 2-methyl-4-trifluoromethyl- 1-(4-methyl-1,3-thiazol-2- 3.04^([a]) 417 1,3-thiazol-5-yl yl)ethyl 181 Me O O 2-methyl-4-trifluoromethyl- (4-methyl-1,3-thiazol-2- 2.58^([a]) 403 1,3-thiazol-5-yl yl)methyl 182 Me O O 2-methyl-4-trifluoromethyl- 1-(5-methyl-1,3-thiazol-2- 3.09^([a]) 417 1,3-thiazol-5-yl yl)ethyl 183 Me O O 2-methyl-4-trifluoromethyl- (5-methyl-1,3-thiazol-2- 2.63^([a]) 403 1,3-thiazol-5-yl yl)methyl 184 Me O O 2-methyl-4-trifluoromethyl- 1,3-benzothiazol-2-ylmethyl 3.15^([a]) 439 1,3-thiazol-5-yl 185 Me O O 2-methyl-4-trifluoromethyl- (4-trifluoromethyl-1,3-thiazol-2- 3.06^([a]) 457 1,3-thiazol-5-yl yl)methyl 186 Et O O 3-bromothiophen-2-yl 1-(tetrahydrofuran-2-yl)ethyl 3.35^([a]) 399 187 Et O O 3-(difluoromethyl)-1-methyl- 1-(2,4-dimethyl-1,3-thiazol-5- 2.43^([a]) 410 1H-pyrazol-4-yl yl)ethyl 188 Et O O 3-(difluoromethyl)-1-methyl- 1-(4-methyl-1,3-thiazol-2- 2.65^([a]) 396 1H-pyrazol-4-yl yl)ethyl 189 Et O O 3-(difluoromethyl)-1-methyl- (4-methyl-1,3-thiazol-2- 2.3^([a]) 382 1H-pyrazol-4-yl yl)methyl 190 Et O O 3-(difluoromethyl)-1-methyl- 1-(5-methyl-1,3-thiazol-2- 2.68^([a]) 396 1H-pyrazol-4-yl yl)ethyl 191 Et O O 3-(difluoromethyl)-1-methyl- 1,3-benzothiazol-2-ylmethyl 2.82^([a]) 418 1H-pyrazol-4-yl 192 Et O O 3-(difluoromethyl)-1-methyl- (4-trifluoromethyl-1,3-thiazol-2- 2.78^([a]) 436 1H-pyrazol-4-yl yl)methyl 193 Et O O 2-methyl-4-trifluoromethyl- 1-(tetrahydrofuran-2-yl)ethyl 3.29^([a]) 404 1,3-thiazol-5-yl 194 Et O O 2-methyl-4-trifluoromethyl- 1-(4-methyl-1,3-thiazol-2- 3.42^([a]) 431 1,3-thiazol-5-yl yl)ethyl 195 Et O O 2-methyl-4-trifluoromethyl- (4-methyl-1,3-thiazol-2- 2.9^([a]) 417 1,3-thiazol-5-yl yl)methyl 196 Et O O 2-methyl-4-trifluoromethyl- 1-(5-methyl-1,3-thiazol-2- 3.46^([a]) 431 1,3-thiazol-5-yl yl)ethyl 197 Et O O 2-methyl-4-trifluoromethyl- 1,3-benzothiazol-2-ylmethyl 3.48^([a]) 453 1,3-thiazol-5-yl 198 Et O O 2-methyl-4-trifluoromethyl- (4-trifluoromethyl-1,3-thiazol-2- 3.35^([a]) 471 1,3-thiazol-5-yl yl)methyl 199 Et O O 3-(difluoromethyl)-1-methyl- 1-(tetrahydrofuran-2-yl)ethyl 2.58^([a]) 369 1H-pyrazol-4-yl 200 Et O O 3-bromothiophen-2-yl (5-fluoropyridin-2-yl)methyl 3.04^([a]) 410 201 Et O O 3-(trifluoromethyl)thiophen- (5-fluoropyridin-2-yl)methyl 3.19^([a]) 400 2-yl 202 Me O O 2-methyl-4-trifluoromethyl- (5-fluoropyridin-2-yl)methyl 2.67^([a]) 401 1,3-thiazol-5-yl 203 Et O O 3-(difluoromethyl)-1-methyl- (5-fluoropyridin-2-yl)methyl 2.33^([a]) 380 1H-pyrazol-4-yl 204 Et O O 2-methyl-4-trifluoromethyl- (5-fluoropyridin-2-yl)methyl 2.98^([a]) 415 1,3-thiazol-5-yl 205 allyl O O 3-bromothiophen-2-yl 1-(1,3-thiazol-2-yl)ethyl 3.31^([a]) 424 206 H O O 3-bromothiophen-2-yl 1-(1,3-thiazol-2-yl)ethyl 382* 207 Et O O 2-methoxypyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 208 Et O O 3,6-dichloropyridin-2-yl 1-(1,3-thiazol-2-yl)ethyl 3.02^([a]) 397 209 Et O O 3-(trifluoromethyl)thiophen- 1-(2-thienyl)ethyl 3.99^([a]) 401 2-yl 210 Me O O 2-methyl-4-trifluoromethyl- 1-(2-thienyl)ethyl 3.46^([a]) 402 1,3-thiazol-5-yl 211 Et O O 3-bromothiophen-2-yl 1-(2-thienyl)ethyl 3.92^([a]) 411 212 Et O O 2-methyl-4-trifluoromethyl- 1-(2-thienyl)ethyl 3.8^([a]) 416 1,3-thiazol-5-yl 213 Et O O 3-(difluoromethyl)-1-methyl- 1-(2-thienyl)ethyl 3.02^([a]) 381 1H-pyrazol-4-yl 214 iPr NH O 3-bromothiophen-2-yl 1-(1,3-thiazol-2-yl)ethyl 3.11^([a]) 425 215 Et O O 3-bromothiophen-2-yl 1-(2,4-dimethyl-1,3-thiazol-5- 3.23^([a]) 440 yl)ethyl 216 Et O O 3-(trifluoromethyl)thiophen- 1-(5-methyl-1,3-thiazol-2- 3.67^([a]) 416 2-yl yl)ethyl 217 Et O O 3-(trifluoromethyl)thiophen- (5-methyl-1,3-thiazol-2- 3.19^([a]) 402 2-yl yl)methyl 218 Et O O 2-methyl-4-trifluoromethyl- 1-(2,4-dimethyl-1,3-thiazol-5- 3.13^([a]) 445 1,3-thiazol-5-yl yl)ethyl 219 Et O O 2-methyl-4-trifluoromethyl- (5-methyl-1,3-thiazol-2- 3^([a]) 417 1,3-thiazol-5-yl yl)methyl 220 Et O O 3-bromothiophen-2-yl (5-methyl-1,3-thiazol-2- 3.04^([a]) 412 yl)methyl 221 Et O O 2,5-dichlorothiophen-3-yl 1-(1,3-thiazol-2-yl)ethyl 3.65^([a]) 402 222 Et O O 2,5-dichlorothiophen-3-yl 1-(pyridin-2-yl)ethyl 2.41^([a]) 396 223 Et O O 4,6-dichloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 3^([a]) 397 224 Et O O 3-bromopyridin-2-yl 1-(1,3-thiazol-2-yl)ethyl 2.53^([a]) 407 225 Et O O 3,5-dichloropyridin-2-yl 1-(1,3-thiazol-2-yl)ethyl 3.11^([a]) 397 226 Et O O 3,6-dichloropyridin-2-yl 1,3-thiazol-2-ylmethyl 2.6^([a]) 383 227 Et O O 4,6-dichloropyridin-3-yl 1,3-thiazol-2-ylmethyl 2.68^([a]) 383 228 Et O O 3,5-dichloropyridin-2-yl 1,3-thiazol-2-ylmethyl 2.7^([a]) 229 Et O O 3-methoxy-1-methyl-1H- 1-(1,3-thiazol-2-yl)ethyl 2.26^([a]) 362 pyrazol-4-yl 230 Et O O 3-(trifluoromethyl)pyridin-2- 1-(1,3-triazol-2-yl)ethyl 2.78^([a]) yl 231 Et O O 2-chloropyridin-3-yl 2-oxotetrahydrofuran-3-yl 1.83^([c]) I2; 1.69^([c]) I1; 1.77^([b]) 232 Et O O 2-(trifluoromethyl)pyridin-3- 1-(1,3-thiazol-2-yl)ethyl 2.9^([a]) 397 yl 233 Et O O 2-(trifluoromethyl)pyridin-3- 1-(pyridin-2-yl)ethyl 2.88^([a]) 391 yl 234 Et O O 5-chloro-3-(difluoromethyl)- 1-(1,3-thiazol-2-yl)ethyl 2.77^([a]) 416 1-methyl-1H-pyrazol-4-yl 235 Et O O 5-chloro-3-(difluoromethyl)- 1-(4,5-dimethyl-1,3-thiazol-2- 3.37^([a]) 444 1-methyl-1H-pyrazol-4-yl yl)ethyl 236 Et O O 5-chloro-3-(difluoromethyl)- 1,3-thiazol-2-ylmethyl 2.4^([a]) 402 1-methyl-1H-pyrazol-4-yl 237 Et O O 5-chloro-3-(difluoromethyl)- 1-(1H-indol-3-yl)propan-2-yl 3.42^([a]) 462 1-methyl-1H-pyrazol-4-yl 238 Et O O 3-ethenyl-1-methyl-1H- 1-(1,3-thiazol-2-yl)ethyl 2.3^([a]) 358 pyrazol-4-yl 239 Et O O 2-chloropyridin-3-yl 2-oxopiperidin-3-yl 1.67^([c];) 1.6^([b]) 240 Et O O 5-bromo-2-(methylsulfanyl) 1-(1,3-thiazol-2-yl)ethyl 3.21^([a]) pyrimidin-4-yl 241 Et O O 2-chloropyridin-3-yl (1S)-1-[(4-ethoxycarbonyl)-1,3- 2.79^([c]) T2; 2.61^([c]) T1; 2.7^([b]) thiazol-2-yl]ethyl 242 Et O O 2,4-dichloro-1,3-thiazol-5-yl 1-(1,3-thiazol-2-yl)ethyl 3.27^([a]) 403 243 2,4-dichloro-1,3-thiazol-5-yl 1-(pyridin-2-yl)ethyl 2.13^([a]) 397 244 Et O O 2-chloropyridin-3-yl (1S)-1-[(4-carboxy)-1,3-thiazol-2- 1.94^([c]) I2; 1.75^([c]) I1; 1.1^([b]) yl]ethyl 245 Et O O 2-chloropyridin-3-yl (1-S)-1-(1,3-thiazol-2-yl)ethyl 246 Et O O 2-bromothiophen-3-yl (4-methyl-1,3-thiazol-2- 2.94^([a]) 413 yl)methyl 247 Et O O 2-bromothiophen-3-yl (5-methyl-1,3-thiazol-2- 3^([a]) 413 yl)methyl 248 Et O O 2-bromothiophen-3-yl 1,3-benzothiazol-2-ylmethyl 3.55^([a]) 449 249 Et O O 2-bromothiophen-3-yl (4-trifluoromethyl-1,3-thiazol-2- 3.42^([a]) 467 yl)methyl 250 Et O O 2-bromothiophen-3-yl 1-(2-thienyl)ethyl 3.99^([a]) 412 251 Et O O 2-bromothiophen-3-yl (5-fluoropyridin-2-yl)methyl 3.04^([a]) 411 252 Et O O 2,5-dichloropyridin-4-yl 1-(1,3-thiazol-2-yl)ethyl 3.15^([a]) 397 253 Et O O 2,5-dichloropyridin-4-yl 1-(3-isopropyl-1,2,4-oxadiazol- 2.2[a] 425 5-yl)ethyl 254 Et O O 2,5-dichloropyridin-4-yl 1-(3-trifluoromethyl-1,2,4- 3.83^([a]) 450 oxadiazol-5-yl)ethyl 255 Et O O 2,5-dichloropyridin-4-yl 1-(1,4-dimethyl-5-oxo-4,5-dihydro- 3.76^([a]) 425 1H-1,2,4-triazol-3-yl)ethyl 256 Et O O 4-(trifluoromethyl)pyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.7^([a]) 397 257 Et O O 4-bromopyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.88^([a]) 407 258 Et O O 4-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.78^([a]) 363 259 Et O O 3-chloropyridin-4-yl 1,3-thiazol-2-ylmethyl 2.11^([a]) 349 260 Et O O 3-chloropyridin-4-yl 1-(pyridin-2-yl)ethyl 2.54^([a]) 357 261 Et O O 2-bromothiophen-3-yl 1-(2,4-dimethyl-1,3-thiazol-5- 2.9^([a]) 440 yl)ethyl 262 Et O O 2-chloropyridin-3-yl 1-(4-{[1-(4- methylphenyl)ethyl]carbamoyl}- 1,3-thiazol-2-yl)ethyl] 263 Et O O 2-(difluoromethyl)pyridin-3-yl 1-(1-methyl-1H-pyrazol-3- 2.18^([a]) 376 yl)ethyl 264 Et O O 2-(difluoromethyl)pyridin-3-yl 1-(pyridin-2-yl)ethyl 2.46^([a]) 373 265 Et O O 4,6-dichloropyridin-2-yl 1-(1,3-thiazol-2-yl)ethyl 3.31^([a]) 397 266 Et O O 2-(difluoromethyl)pyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.39^([a]) 379 267 propargyl O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.19^([c]) T1; 2.31^([c]) T2; 2.26^([b]) 268 cBu O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 3^([c]) T2; 2.79^([c]) T1; 2.88^([b]) 269 Me NH O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 1.63^([c]) T1; 1.76^([c]) T2; 1.69^([b]) 270 Et O O 1-methyl-4-(trifluoromethyl)- 1-(pyridin-2-yl)ethyl 2.92^([a]) 393 1H-pyrrol-3-yl 271 Et O O 1-methyl-4-(trifluoromethyl)- 1-(1,3-thiazol-2-yl)ethyl 2.97^([a]) 399 1H-pyrrol-3-yl 272 Et O O 4-(trifluoromethyl)pyridin-3-yl 1,3-thiazol-2-ylmethyl 2.4^([a]) 273 Et O O 2-chloropyridin-3-yl 1-(piperidin-1-yl)propan-2-yl 1.2^([a]) 377 274 Et O O 2-chloropyridin-3-yl 1-(morpholin-4-yl)propan-2-yl 1.3^([a]) 379 275 Et O O 2-chloropyridin-3-yl 1-(1,3-thiazol-4-yl)ethyl 2.4^([a]) 363 276 Et O O 2-chloropyridin-3-yl 1-(1-methyl-1H-pyrazol-3- 2.3^([a]) 360 yl)ethyl 277 Et O O 2-chloropyridin-3-yl 1-(1,3,5-trimethyl-1H-pyrazol-4- 2.3^([a]) 388 yl)ethyl 278 Et O O 2-chloropyridin-3-yl 1-(1H-pyrazol-1-yl)propan-2-yl 2.23^([a]) 360 279 Et O O 2-chloropyridin-3-yl 1-(1H-benzimidazol-2-yl)ethyl 2^([a]) 396 280 Et O O 2-chloropyridin-3-yl 1-(2-methyl-4,5,6,7-tetrahydro- 4.4^([a]) 430 1-benzothiophen-3-yl)ethyl 281 Et O O 2-chloropyridin-3-yl 1-(5-chlorothiophen-2-yl)ethyl 3.8^([a]) 282 Et O O 2-chloropyridin-3-yl 1-[3-(propan-2-yl)-1,2,4- 3.2^([a]) 390 oxadiazol-5-yl]ethyl 283 Et O O 2-chloropyridin-3-yl 1-(pyrrolidin-1-yl)propan-2-yl 3.35^([a]) 284 Et O O 2-chloropyridin-3-yl 1-(pyridin-2-yl)cyclopropyl 2.56^([a]) 285 Et O O 2-chloropyridin-3-yl 1-[5-(trifluoromethyl)pyridin-2- 3.5^([a]) yl]ethyl 286 Et O O 2-chloropyridin-3-yl 2-hydroxypyridin-3-yl 1.9^([a]) 345 287 Et O O 2-chloropyridin-3-yl 1-(5-bromo-3-chloropyridin-2- 3.9^([a]) 469 yl)ethyl 288 Et O O 2-chloropyridin-3-yl 1-[3-chloro-5-(trifluoromethyl)- 3.9^([a]) 460 pyridin-2-yl]ethyl 289 Et O O 2,3-dichloropyridin-4-yl 1-(pyridin-2-yl)ethyl 3.04^([a]) 392 290 Et O O 2,3-dichloropyridin-4-yl 1-(1,3-thiazol-4-yl)ethyl 2.92^([a]) 398 291 Et O O 2,3-dichloropyridin-4-yl 1-(1,3-thiazol-2-yl)ethyl 2.96^([a]) 398 292 Et O O 2-chloropyridin-3-yl 1-(pyridin-2-yl)ethyl 2.5^([a]) 357 293 Et O O 2-chloropyridin-3-yl 3-methylpyridin-4-yl 1.45^([a]) 343 294 Et O O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)propan-2-yl 2.4^([a]) 377 295 Et O O 2-chloropyridin-3-yl 1-(pyridin-2-yl)propan-2-yl 1.82^([a]) 371 296 Et O O 2-chloropyridin-3-yl 1-(pyridin-3-yl)propan-2-yl 1.57^([a]) 371 297 Et O O 3-bromopyridin-4-yl 1-(1,3-thiazol-2-yl)ethyl 2.4^([a]) 298 Et O O 3-bromopyridin-4-yl 1-(1,3-thiazol-4-yl)ethyl 2.4^([a]) 407 299 Et O O 3-bromopyridin-4-yl 1-(pyridin-2-yl)ethyl 2.5^([a]) 401 300 Et O O 3-fluoropyridin-4-yl 1-(pyridin-2-yl)ethyl 2.28^([a]) 341 301 Et O O 3-fluoropyridin-4-yl 1-(1,3-thiazol-4-yl)ethyl 2.22^([a]) 347 302 Et O O 3-fluoropyridin-4-yl 1-(1,3-thiazol-2-yl)propan-2-yl 2.19^([a]) 361 303 Et O O 3-(trifluoromethyl)pyridin-4-yl 1-(1,3-thiazol-4-yl)ethyl 2.6^([a]) 397 304 Et O O 2-chloropyridin-3-yl 1-[4-(dimethylcarbamoyl)-1,3- 1.98^([c]) T1; 2.18^([c]) T2; 2.08^([b]) thiazol-2-yl]ethyl 305 allyl O O 3-(difluoromethyl)-1-methyl- 1-(1,3-thiazol-2-yl)ethyl 2.59^([a]) 394 1H-pyrazol-4-yl 306 allyl O O 3-(difluoromethyl)-1-methyl- 1,3-thiazol-2-ylmethyl 2.25^([a]) 380 1H-pyrazol-4-yl 307 allyl O O 3-(difluoromethyl)-1-methyl- 1-(pyridin-2-yl)ethyl 2.56^([a]) 388 1H-pyrazol-4-yl 308 Et O O 5-fluoro-1-methyl-3-(trifluoro- 1-(1,3-thiazol-2-yl)ethyl 3.09^([a]) 418 methyl)-1H-pyrazol-4-yl 309 Et O O 3-(difluoromethyl)-5-fluoro- 1-(1,3-thiazol-2-yl)ethyl 2.73^([a]) 400 1-methyl-1H-pyrazol-4-yl 310 Et O O 5-fluoro-1-methyl-3-(trifluoro- 1-(pyridin-2-yl)ethyl 3.12^([a]) 412 methyl)-1H-pyrazol-4-yl 311 Et O O 5-chloro-1-methyl-3-(trifluoro- 1-(1,3-thiazol-2-yl)ethyl 3.2^([a]) 434 methyl)-1H-pyrazol-4-yl 312 Et O O 3-(1,1-difluoroethyl)-1- 1-(1,3-thiazol-2-yl)ethyl 2.62^([a]) 396 methyl-1H-pyrazol-4-yl 313 Et O O 2-chloropyridin-3-yl 1-[4-(ethylcarbamoyl)-1,3- thiazol-2-yl]ethyl 314 Et O O 5-chloro-1-methyl-3-(trifluoro- 1-(pyridin-2-yl)ethyl 3.24^([a]) 428 methyl)-1H-pyrazol-4-yl 315 Et O O 3-(1,1-difluoroethyl)-1- 1-(pyridin-2-yl)ethyl 2.57^([a]) 390 methyl-1H-pyrazol-4-yl 316 Et O O 3-(difluoromethyl)-5-fluoro- 1-(pyridin-2-yl)ethyl 2.73^([a]) 394 1-methyl-1H-pyrazol-4-yl 317 propargyl NH O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.03^([a]) 372 318 Et O O 3-fluoropyridin-4-yl 1-(1,3-thiazol-2-yl)ethyl 2.41^([a]) 347 319 Et O O 2-chloropyridin-3-yl 2-phenyl-1,3-thiazol-4- 3.63^([a]) 425 yl)methyl 320 Et O O 2-chloropyridin-3-yl 1-(pyridin-4-yl)propan-2-yl 1.64^([a]) 321 Et O O 2-chloropyridin-3-yl 1-(1-methyl-1H-pyrazol-4- 2.2^([a]) 360 yl)ethyl 322 Et O O 2-chloropyridin-3-yl 1-(2-chloro-1,3-thiazol-4-yl)ethyl 3.3^([a]) 397 323 Et O O 2-chloropyridin-3-yl quinolin-2-ylmethyl 3.13^([a]) 324 CH₂CF₃ NH O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.44^([a]) 416 325 Et O O 3-(difluoromethyl)-1-methyl- 1-(pyridin-2-yl)ethyl 2.39^([a]) 376 1H-pyrazol-4-yl 326 Et O O 3-(difluoromethyl)-1-methyl- 1-(1,3-thiazol-2-yl)ethyl 2.44^([a]) 382 1H-pyrazol-4-yl 327 2-MeOEt NH O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 1.93^([a]) 392 328 Et NH O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.07^([a]); 1.94^([c]) T1; 2.1^([c]) T2; 2.05^([b]) 362 329 Et O O 2-chloropyridin-3-yl 1-(pyrimidin-2-yl)ethyl 2.13^([a]) 358 330 Et O O 2-chloropyridin-3-yl 1-(pyrimidin-4-yl)ethyl 2.01^([a]) 358 331 Et O O 2-chloropyridin-3-yl 2-(1,3-thiazol-2-yl)propyl 2.57^([a]) 377 332 Me O O 2-chloropyridin-3-yl 1-(4-chlorophenyl)ethyl 3.24^([a]) 333 Me O O 2-chloropyridin-3-yl 3-chlorophenyl 334 Me O O 2-chloropyridin-3-yl 2-(methylsulfanyl)phenyl 2.82^([c]); 2.82^([b]) 335 Me O O 2-chloropyridin-3-yl 2-methoxyphenyl 2.58^([c]); 2.56^([b]) 336 Me O O 2-chloropyridin-3-yl 4-chlorobenzyl 2.98^([c]); 2.96^([b]) 337 Me O O 2-chloropyridin-3-yl 2-(4-chlorophenyl)propan-2-yl 3.33^([a]) 338 Me O O 2-chloropyridin-3-yl (6-chloropyridin-3-yl)methyl 2.11^([c]); 2.1^([b]) 339 Me O O 2-chloropyridin-3-yl 3-(methylsulfanyl)phenyl 3.04^([c]); 2.83^([b]) 340 Me O O 2-chloropyridin-3-yl 2-(ethylsulfanyl)phenyl 341 Et O O 2-chloropyridin-3-yl 2-(methylsulfanyl)phenyl 3.32^([c]); 3.17^([b]) 342 Et O O 2-chloropyridin-3-yl 1-(4-chlorophenyl)ethyl 3.88^([c]) T2; 3.68^([c]) T1; 3.61^([b]) 343 Et O O 2-chloro-6-methylpyridin-3-yl 2-(methylsulfanyl)phenyl 3.57^([c]); 3.41^([b]) 344 CH₂CF₃ O O 2-chloropyridin-3-yl 2-(methylsulfanyl)phenyl 3.55^([c]); 3.21^([b]) 345 Et O O 2-chloropyridin-3-yl (1R)-1-(4-chlorophenyl)ethyl 3.69^([c]) T1; 3.88^([c]) T2; 3.63^([b]) 346 Et O O 2,5-dichloropyridin-3-yl 2-(methylsulfanyl)phenyl 3.94^([c]); 3.7^([b]) 347 iBu O O 2-chloropyridin-3-yl 2-(methylsulfanyl)phenyl 4.15^([c]); 3.94^([b]) 348 Et O O 3-(difluoromethyl)-1-methyl- 1-(4-chlorophenyl)ethyl 3.6^([a]) 409 1H-pyrazol-4-yl 349 Et O O 3-(difluoromethyl)-1-methyl- 2-(methylsulfanyl)phenyl 3.13^([a]) 393 1H-pyrazol-4-yl 350 Et O O 3-chloro-5-(trifluoromethyl)- 2-(methylsulfanyl)phenyl 4.26^([a]) 442 pyridin-2-yl 351 Et O O 3-chloro-5-(trifluoro- 1-(4-chlorophenyl)ethyl 4.56^([a]) 458 methyl)pyridin-2-yl 352 Et O O 5-fluoro-1,3-dimethyl-1H- 1-(4-chlorophenyl)ethyl 3.62^([a]) 391 pyrazol-4-yl 353 Me O O 2-chloropyridin-3-yl 2,2,2-trifluoro-1-phenylethyl 354 Et O O 5-fluoro-1,3-dimethyl-1H- 2-(methylsulfanyl)phenyl 3.21^([a]) 375 pyrazol-4-yl 355 Et O O 4,5-dichloro-1,2-thiazol-3-yl 1-(4-chlorophenyl)ethyl 4.65^([a]) 430 356 Me O O 3-(difluoromethyl)-1-methyl- 1-(4-chlorophenyl)ethyl 3.31^([a]) 395 1H-pyrazol-4-yl 357 Me O O 3-(difluoromethyl)-1-methyl- 2-(methylsulfanyl)phenyl 2.8^([a]) 379 1H-pyrazol-4-yl 358 Et O O 4,5-dichloro-1,2-thiazol-3-yl 2-(methylsulfanyl)phenyl 4.31^([a]) 414 359 Me O O 2-chloropyridin-3-yl 2-(cyclopropylcarbonyl)phenyl 360 Et O O 2,6-dichloropyridin-3-yl 2-(methylsulfanyl)phenyl 3.97^([c]); 3.79^([b]) 361 Et O O 2-chloropyridin-3-yl 2-(1,1,1,3,3,3-hexafluoro-2- hydroxypropan-2-yl)phenyl 362 Et O O 3-methylisoxazol-4-yl 1-(4-chlorophenyl)ethyl 3.62^([a]) 360 363 Et O O 3-methylisoxazol-4-yl 2-(methylsulfanyl)phenyl 3.21^([a]) 344 364 Et O O 2-chloropyridin-3-yl biphenyl-2-yl 365 Et O O 3-bromothiophen-2-yl 1-(4-chlorophenyl)ethyl 4.42^([a]) 439 366 Et O O 3-bromothiophen-2-yl 2-(methylsulfanyl)phenyl 3.96^([a]) 423 367 Et O O 5-chloro-1,3-dimethyl-1H- 1-(4-chlorophenyl)ethyl 3.8^([a]) 407 pyrazol-4-yl 368 Et O O 3-(trifluoromethyl)thiophen- 1-(4-chlorophenyl)ethyl 4.47^([a]) 429 2-yl 369 Et O O 3-(trifluoromethyl)thiophen- 2-(methylsulfanyl)phenyl 4.01^([a]) 413 2-yl 370 Me O O 2-chloropyridin-3-yl 2-phenylpropan-2-yl 2.98^([a]) 371 Me O O 2-chloropyridin-3-yl 1-(pyridin-4-yl)ethyl 1.24^([a]) 372 Me O O 2-chloropyridin-3-yl 1-(3-chlorophenyl)propyl 3.58^([a]) 373 Me O O 2-chloropyridin-3-yl 1-(2-methylphenyl)ethyl 3.15^([a]) 374 Me O O 2-chloropyridin-3-yl 1-(2,4-dichlorophenyl)ethyl 3.73^([a]) 375 Me O O 2-chloropyridin-3-yl 1-(2-chlorophenyl)ethyl 3.19^([a]) 376 Me O O 2-chloropyridin-3-yl 1-(4-chlorophenyl)propyl 3.58^([a]) 377 Me O O 2-chloropyridin-3-yl 1-(3-methoxyphenyl)ethyl 2.89^([a]) 378 Me O O 2-chloropyridin-3-yl 1-(4-ethoxyphenyl)ethyl 3.02^([a]) 379 Me O O 2-chloropyridin-3-yl 1-(4-isopropylphenyl)ethyl 4^([a]) 380 Me O O 2-chloropyridin-3-yl 1-(2,6- difluorophenyl)cyclopropyl 2.8^([a]) 381 Me O O 2-chloropyridin-3-yl (4-chloro- 3.58^([a]) phenyl)(cyclopropyl)methyl 382 Me O O 2-chloropyridin-3-yl 1-(2-chlorophenyl)cyclopropyl 2.61^([a]) 383 Me O O 2-chloropyridin-3-yl 1-(3-chlorophenyl)cyclopropyl 3.11^([a]) 384 Me O O 2-chloropyridin-3-yl 1-(4-chlorophenyl)cyclopropyl 3.19^([a]) 385 Me O O 2-chloropyridin-3-yl 2-(2,6-difluorophenyl)propan-2-yl 2.98^([a]) 386 Me O O 2-chloropyridin-3-yl 2-(4-methoxyphenyl)propan-2-yl 3.02^([a]) 387 Me O O 2-chloropyridin-3-yl 1-(3,4-dichlorophenyl)ethyl 3.58^([a]) 388 Me O O 2-chloropyridin-3-yl 1-(3,5-dichlorophenyl)ethyl 3.68^([a]) 389 Me O O 2-chloropyridin-3-yl 3,3,3-trifluoro-1-phenylpropyl 2.98^([a]) 390 Me O O 2-chloropyridin-3-yl (3-chlorophenyl)(cyclopropyl)- 2.93^([a]) methyl 391 Me O O 2-chloropyridin-3-yl 1-(2-methoxyphenyl)propyl 3.15^([a]) 392 Me O O 2-chloropyridin-3-yl 1-(2-methoxyphenyl)ethyl 2.84^([a]) 393 Me O O 2-chloropyridin-3-yl 2-(2-chlorophenyl)propan-2-yl 3.15^([a]) 394 Me O O 2-chloropyridin-3-yl 1-(2,5-dichlorophenyl)ethyl 3.28^([a]) 395 Me O O 2-chloropyridin-3-yl 1-(4-trifluoromethylphenyl)ethyl 3.37^([a]) 396 Me O O 2-chloropyridin-3-yl 1-(3-methylphenyl)ethyl 3.02^([a]) 397 Me O O 2-chloropyridin-3-yl 1-(4-fluorophenyl)ethyl 2.89^([a]) 398 Me O O 2-chloropyridin-3-yl (phenyl)(cyclopropyl)methyl 3.24^([a]) 399 Me O O 2-chloropyridin-3-yl 2-(4-fluorophenyl)propan-2-yl 2.98^([a]) 400 Me O O 2-chloropyridin-3-yl 1-(3,4-dimethoxyphenyl)ethyl 2.34^([a]) 401 Me O O 2-chloropyridin-3-yl 1-(3-trifluoromethylphenyl)ethyl 3.28^([a]) 402 Me O O 2-chloropyridin-3-yl 1-(1,3-benzodioxol-5-yl)ethyl 2.53^([a]) 403 Me O O 2-chloropyridin-3-yl 1-(3-chlorophenyl)ethyl 3.19^([a]) 404 Me O O 2-chloropyridin-3-yl 1-phenylethyl 2.89^([a]) 405 Me O O 2-chloropyridin-3-yl 1-phenylpropyl 3.02^([a]) 406 Me O O 2-chloropyridin-3-yl 1-(4-tert-butylphenyl)ethyl 4.23^([a]) 407 Me O O 2-chloropyridin-3-yl 1-(4-ethylphenyl)ethyl 3.63^([a]) 408 Me O O 2-chloropyridin-3-yl 1-(4-methoxyphenyl)ethyl 2.65^([a]) 409 Me O O 2-chloropyridin-3-yl 1-(4-methylphenyl)ethyl 3.28^([a]) 410 Et O O 5-chloro-1,3-dimethyl-1H- 2-(methylsulfanyl)phenyl 3.42^([a]) 391 pyrazol-4-yl 411 Et O O 2-bromothiophen-3-yl 1-(4-chlorophenyl)ethyl 4.35^([a]) 439 412 Et O O 2-bromothiophen-3-yl 2-(methylsulfanyl)phenyl 3.99^([a]) 423 413 Et O O 2-chloropyridin-3-yl 2-(methylsulfanyl)-5- (trifluoromethyl)phenyl 414 Et O O 2,5-dimethylfuran-3-yl 2-(methylsulfanyl)phenyl 3.84^([a]) 415 Et O O 2,5-dimethylfuran-3-yl 2-[(pentafluoroethyl)- 4.7^([a]) sulfanyl]phenyl 416 Et O O 2,5-dimethylfuran-3-yl 2-[(trifluoroethyl)- 4.3^([a]) sulfanyl]phenyl 417 Et O O 2,5-dimethylfuran-3-yl 2-(methylsulfonyl)phenyl 2.65^([a]) 418 Et O O 2,5-dimethylfuran-3-yl 2-[(2-chloro-1,1,2-trifluoroethyl)- 4.25^([a]) sulfanyl]phenyl 419 Et O O 2,5-dimethylfuran-3-yl 2-[(4-methylphenyl)sulfa- 5.08^([a]) nyl]phenyl 420 Et O O 2,5-dimethylfuran-3-yl 2-(prop-2-en-1-ylsulfanyl)phenyl 4.25^([a]) 421 Et O O 2,5-dimethylfuran-3-yl 2-(propan-2-ylsulfanyl)phenyl 4.57^([a]) 422 Et O O 2,5-dimethylfuran-3-yl 2-bromophenyl 3.99^([a]) 423 Me O O 2-chloropyridin-3-yl 1-(2-methylphenyl)propan-2-yl 3.23^([a]) 424 Me O O 2-chloropyridin-3-yl 4-phenylbutan-2-yl 3.27^([a]) 425 Me O O 2-chloropyridin-3-yl 4-(3-methylphenyl)butan-2-yl 3.68^([a]) 426 Me O O 2-chloropyridin-3-yl 1-phenylpropan-2-yl 2.98^([a]) 427 Me O O 2-methyl-4-trifluoromethyl- 1-(4-chlorophenyl)ethyl 3.98^([a]) 430 1,3-thiazol-5-yl 428 Me O O 2-methyl-4-trifluoromethyl- 2-(methylsulfanyl)phenyl 3.46^([a]) 414 1,3-thiazol-5-yl 429 Et O O 2-chloropyridin-3-yl 4-(2,6-dichlorophenyl)butan-2-yl 4.69^([c]) I2; 4.58^([c]) I1; 4.62^([b]) 430 Et O O 1-methyl-3-(trifluoromethyl)- 1-(4-chlorophenyl)ethyl 3.95^([a]) 427 1H-pyrazol-4-yl 431 Et O O 1-methyl-3-(trifluoromethyl)- 2-(methylsulfanyl)phenyl 3.48^([a]) 411 1H-pyrazol-4-yl 432 Et O O 2-methyl-4-trifluoromethyl- 2-(methylsulfanyl)phenyl 3.8^([a]) 428 1,3-thiazol-5-yl 433 Et O O 2-methyl-4-trifluoromethyl- 1-(4-chlorophenyl)ethyl 4.27^([a]) 1,3-thiazol-5-yl 434 Et O O 3-chlorothiophen-2-yl 1-(4-chlorophenyl)ethyl 4.4^([a]) 395 435 Et O O 3-chlorothiophen-2-yl 2-(methylsulfanyl)phenyl 3.92^([a]) 379 436 Et O O 2-iodothiophen-3-yl 2-(methylsulfanyl)phenyl 3.94^([a]) 471 437 Et O O 3-(trifluoromethyl)thiophen- 4-phenylbutan-2-yl 4.56^([a]) 423 2-yl 438 Et O O 3-(trifluoromethyl)thiophen- 1-(4-fluorophenyl)ethyl 4.14^([a]) 413 2-yl 439 Et O O 3-(trifluoromethyl)thiophen- 1-(4-methylphenyl)ethyl 4.54^([a]) 409 2-yl 440 Et O O 3-(trifluoromethyl)thiophen- 1-phenylethyl 4.16^([a]) 395 2-yl 441 Me O O 2-methyl-4-trifluoromethyl- 4-phenylbutan-2-yl 4.01^([a]) 424 1,3-thiazol-5-yl 442 Me O O 2-methyl-4-trifluoromethyl- 1-(4-fluorophenyl)ethyl 3.64^([a]) 414 1,3-thiazol-5-yl 443 Me O O 2-methyl-4-trifluoromethyl- 1-(4-methylphenyl)ethyl 4.01^([a]) 410 1,3-thiazol-5-yl 444 Me O O 2-methyl-4-trifluoromethyl- 1-phenylethyl 3.62^([a]) 396 1,3-thiazol-5-yl 445 Et O O 3-bromothiophen-2-yl 4-phenylbutan-2-yl 4.51^([a]) 433 446 Et O O 3-bromothiophen-2-yl 1-(4-fluorophenyl)ethyl 4.06^([a]) 423 447 Et O O 3-bromothiophen-2-yl 1-(4-methylphenyl)ethyl 4.49^([a]) 419 448 Et O O 3-bromothiophen-2-yl 1-phenylethyl 4.09^([a]) 405 449 Et O O 2-methyl-4-trifluoromethyl- 4-phenylbutan-2-yl 4.36^([a]) 438 1,3-thiazol-5-yl 450 Et O O 2-methyl-4-trifluoromethyl- 1-(4-fluorophenyl)ethyl 3.96^([a]) 428 1,3-thiazol-5-yl 451 Et O O 2-methyl-4-trifluoromethyl- 1-(4-methylphenyl)ethyl 4.36^([a]) 424 1,3-thiazol-5-yl 452 Et O O 2-methyl-4-trifluoromethyl- 1-phenylethyl 3.99^([a]) 410 1,3-thiazol-5-yl 453 Et O O 3-(difluoromethyl)-1-methyl- 4-phenylbutan-2-y 3.62^([a]) 403 1H-pyrazol-4-yl 454 Et O O 3-(difluoromethyl)-1-methyl- 1-(4-fluorophenyl)ethyl 3.21^([a]) 393 1H-pyrazol-4-yl 455 Et O O 3-(difluoromethyl)-1-methyl- 1-(4-methylphenyl)ethyl 3.51^([a]) 389 1H-pyrazol-4-yl 456 Et O O 3-(difluoromethyl)-1-methyl- 1-phenylethyl 3.17^([a]) 375 1H-pyrazol-4-yl 457 Et O O 3-bromothiophen-2-yl 4-chlorophenyl 4.11^([a]) 411 458 Et O O 3-bromothiophen-2-yl 2-(methylsulfanyl)benzyl 4.01^([a]) 437 459 Et O O 3-bromothiophen-2-yl 3-chlorophenyl 4.09^([a]) 411 460 Et O O 3-(trifluoromethyl)thiophen- 2-(propan-2-yloxy)phenyl 4.54^([a]) 425 2-yl 461 Et O O 3-(trifluoromethyl)thiophen- 4-(difluoromethoxy)phenyl 3.78^([a]) 433 2-yl 462 Et O O 3-(trifluoromethyl)thiophen- 4-(methylsulfanyl)phenyl 4.09^([a]) 413 2-yl 463 Et O O 3-(trifluoromethyl)thiophen- 2-(methylsulfanyl)benzyl 4.09^([a]) 427 2-yl 464 Et O O 2-methyl-4-trifluoromethyl- 2-(methylsulfanyl)benzyl 3.87^([a]) 442 1,3-thiazol-5-yl 465 Me O O 2-methyl-4-trifluoromethyl- 1,3-benzothiazol-6-yl 2.64^([a]) 425 1,3-thiazol-5-yl 466 Me O O 2-methyl-4-trifluoromethyl- 2-(methylsulfanyl)benzyl 3.55^([a]) 428 1,3-thiazol-5-yl 467 Et O O 3-bromothiophen-2-yl 2-(propan-2-yloxy)phenyl 4.46^([a]) 435 468 Et O O 3-bromothiophen-2-yl 4-(difluoromethoxy)phenyl 3.73^([a]) 469 Et O O 3-bromothiophen-2-yl 1,3-benzothiazol-6-yl 3.09^([a]) 434 470 Et O O 3-bromothiophen-2-yl 4-(methylsulfanyl)phenyl 4.01^([a]) 423 471 Et O O 3-(difluoromethyl)-1-methyl- 2-(propan-2-yloxy)phenyl 3.53^([a]) 405 1H-pyrazol-4-yl 472 Et O O 3-(difluoromethyl)-1-methyl- 4-(difluoromethoxy)phenyl 3.04^([a]) 413 1H-pyrazol-4-yl 473 Et O O 3-(difluoromethyl)-1-methyl- 1,3-benzothiazol-6-yl 2.44^([a]) 404 1H-pyrazol-4-yl 474 Et O O 3-(difluoromethyl)-1-methyl- 4-(methylsulfanyl)phenyl 3.19^([a]) 393 1H-pyrazol-4-yl 475 Et O O 3-(difluoromethyl)-1-methyl- 4-chlorophenyl 3.23^([a]) 381 1H-pyrazol-4-yl 476 Et O O 3-(difluoromethyl)-1-methyl- 2-(methylsulfanyl)benzyl 3.17^([a]) 407 1H-pyrazol-4-yl 477 Et O O 3-(difluoromethyl)-1-methyl- 3-chlorophenyl 3.21^([a]) 381 1H-pyrazol-4-yl 478 Et O O 2-methyl-4-trifluoromethyl- 4-(difluoromethoxy)phenyl 1,3-thiazol-5-yl 479 Et O O 2-methyl-4-trifluoromethyl- 1,3-benzothiazol-6-yl 2.98^([a]) 439 1,3-thiazol-5-yl 480 Et O O 2-methyl-4-trifluoromethyl- 4-(methylsulfanyl)phenyl 3.87^([a]) 428 1,3-thiazol-5-yl 481 Et O O 3-(trifluoromethyl)thiophen- 4-(propan-2-yl)phenyl 4.75^([a]) 409 2-yl 482 Et O O 3-(trifluoromethyl)thiophen- 3-(methylsulfanyl)phenyl 4.04^([a]) 413 2-yl 483 Et O O 3-(trifluoromethyl)thiophen- 4-methoxyphenyl 3.62^([a]) 397 2-yl 484 Et O O 3-(trifluoromethyl)thiophen- 4-(dimethylamino)phenyl 3.89^([a]) 410 2-yl 485 Me O O 2-methyl-4-trifluoromethyl- 4-methoxyphenyl 3.06^([a]) 398 1,3-thiazol-5-yl 486 Me O O 2-methyl-4-trifluoromethyl- 4-(dimethylamino)phenyl 3.31^([a]) 411 1,3-thiazol-5-yl 487 Me O O 2-methyl-4-trifluoromethyl- 4-(propan-2-yl)phenyl 4.14^([a]) 1,3-thiazol-5-yl 488 Et O O 3-bromothiophen-2-yl 4-methoxyphenyl 3.55^([a]) 407 489 Et O O 3-bromothiophen-2-yl 4-(dimethylamino)phenyl 3.76^([a]) 420 490 Et O O 3-bromothiophen-2-yl 4-(propan-2-yl)phenyl 4.73^([a]) 419 491 Et O O 3-bromothiophen-2-yl 3-(methylsulfanyl)phenyl 3.96^([a]) 423 492 Et O O 2-methyl-4-trifluoromethyl- 4-methoxyphenyl 3.44^([a]) 412 1,3-thiazol-5-yl 493 Et O O 2-methyl-4-trifluoromethyl- 4-(dimethylamino)phenyl 3.71^([a]) 425 1,3-thiazol-5-yl 494 Et O O 2-methyl-4-trifluoromethyl- 4-(propan-2-yl)phenyl 4.54^([a]) 424 1,3-thiazol-5-yl 495 Et O O 3-(difluoromethyl)-1-methyl- 4-methoxyphenyl 2.77^([a]) 377 1H-pyrazol-4-yl 496 Et O O 3-(difluoromethyl)-1-methyl- 4-(dimethylamino)phenyl 2.71^([a]) 390 1H-pyrazol-4-yl 497 Et O O 3-(difluoromethyl)-1-methyl- 4-(propan-2-yl)phenyl 3.76^([a]) 389 1H-pyrazol-4-yl 498 Et O O 3-(difluoromethyl)-1-methyl- 3-(methylsulfanyl)phenyl 3.17^([a]) 393 1H-pyrazol-4-yl 499 Et O O 2,5-dichlorothiophen-3-yl 1-(4-chlorophenyl)ethyl 4.96^([a]) 429 500 Et O O 2,5-dichlorothiophen-3-yl 2-(methylsulfanyl)phenyl 4.59^([a]) 501 Et O O 2,5-dichlorothiophen-3-yl 1-(2,6- 4.62^([a]) 443 difluorophenyl)cyclopropyl 502 Et O O 3,6-dichloropyridin-2-yl 2-(methylsulfanyl)phenyl 3.99^([a]) 408 503 Et O O 3,5-dichloropyridin-2-yl 2-(methylsulfanyl)phenyl 4.09^([a]) 504 Me O O 2-methyl-4-trifluoromethyl- 3-(methylsulfanyl)phenyl 3.53^([a]) 414 1,3-thiazol-5-yl 505 Et O O 2-methyl-4-trifluoromethyl- 3-(methylsulfanyl)phenyl 3.89^([a]) 428 1,3-thiazol-5-yl 506 Et O O 3-methoxy-1-methyl-1H- 1-(4-chlorophenyl)ethyl 3.51^([a]) 389 pyrazol-4-yl 507 Et O O 3-methoxy-1-methyl-1H- 2-(methylsulfanyl)phenyl 3.06^([a]) 373 pyrazol-4-yl 508 Et O O 3-methoxy-1-methyl-1H- 1-(2,6- 3.02^([a]) 403 pyrazol-4-yl difluorophenyl)cyclopropyl 509 Et O O 3-(trifluoromethyl)thiophen- 1,3-benzothiazol-6-yl 3.21^([a]) 424 2-yl 510 Et O O 3-(trifluoromethyl)thiophen- 4-chlorophenyl 4.14^([a]) 401 2-yl 511 Et O O 3-(trifluoromethyl)thiophen- 3-chlorophenyl 414^([a]) 401 2-yl 512 Et O O 2-methyl-4-trifluoromethyl- 4-chlorophenyl 3.92^([a]) 416 1,3-thiazol-5-yl 513 Et O O 2-methyl-4-trifluoromethyl- 3-chlorophenyl 3.89^([a]) 416 1,3-thiazol-5-yl 514 Me O O 2-methyl-4-trifluoromethyl- 2-(propan-2-yloxy)phenyl 3.96^([a]) 426 1,3-thiazol-5-yl 515 Me O O 2-methyl-4-trifluoromethyl- 4-(difluoromethoxy)phenyl 3.31^([a]) 434 1,3-thiazol-5-yl 516 Me O O 2-methyl-4-trifluoromethyl- 4-(methylsulfanyl)phenyl 3.53^([a]) 414 1,3-thiazol-5-yl 517 Me O O 2-methyl-4-trifluoromethyl- 4-chlorophenyl 3.55^([a]) 402 1,3-thiazol-5-yl 518 Me O O 2-methyl-4-trifluoromethyl- 3-chlorophenyl 3.53^([a]) 402 1,3-thiazol-5-yl 519 Et O O 2-methyl-4-trifluoromethyl- 2-(propan-2-yloxy)phenyl 4.36^([a]) 440 1,3-thiazol-5-yl 520 Et O O 3-(1-fluoroethyl)-1-methyl- 1-(4-chlorophenyl)ethyl 3.64^([a]) 1H-pyrazol-4-yl 521 Et O O 3-(1-fluoroethyl)-1-methyl- 2-(methylsulfanyl)phenyl 3.15^([a]) 389 1H-pyrazol-4-yl 522 Et O O 2-methoxypyridin-3-yl 2-(methylsulfanyl)phenyl 3.32^([c]); 3.32^([b]) 523 Et O O 2-bromothiophen-3-yl 2-(propan-2-yloxy)phenyl 4.46^([a]) 435 524 Et O O 2-bromothiophen-3-yl 4-(methylsulfanyl)phenyl 4.01^([a]) 422 525 Et O O 2-bromothiophen-3-yl 4-methoxyphenyl 3.6^([a]) 407 526 Et O O 2,4-dichloro-1,3-thiazol-5-yl 1-(4-chlorophenyl)ethyl 4.54^([a]) 430 527 Et O O 2,4-dichloro-1,3-thiazol-5-yl 2-(methylsulfanyl)phenyl 4.14^([a]) 414 528 Et O O 2,4-dichloro-1,3-thiazol-5-yl 1-(2,6- 4.14^([a]) 444 difluorophenyl)cyclopropyl 529 Et O O 2-chloropyridin-3-yl 2-(trifluoromethoxy)phenyl 3.52^([c]); 3.46^([b]) 530 Et O O 1-methyl-3-(trifluoromethyl)- 1-(2,6- 3.48^([a]) 441 1H-pyrazol-4-yl difluorophenyl)cyclopropyl 531 Et O O 2-bromothiophen-3-yl 1-(4-fluorophenyl)ethyl 3.89^([a]) 423 532 Et O O 2-bromothiophen-3-yl 4-(difluoromethoxy)phenyl 3.73^([a]) 444 533 Et O O 2-bromothiophen-3-yl 1,3-benzothiazol-6-yl 3.11^([a]) 435 534 Et O O 2-bromothiophen-3-yl 4-chlorophenyl 4.11^([a]) 412 535 Et O O 2-bromothiophen-3-yl 2-(methylsulfanyl)benzyl 4.01^([a]) 438 536 Et O O 2-bromothiophen-3-yl 4-(propan-2-yl)phenyl 4.78^([a]) 420 537 Et O O 2-bromothiophen-3-yl 3-(methylsulfanyl)phenyl 4.04^([a]) 424 538 Et O O 2-bromothiophen-3-yl 4-phenylbutan-2-yl 4.56^([a]) 434 539 Et O O 2-bromothiophen-3-yl 3-chlorophenyl 4.09^([a]) 412 540 Et O O 2-bromothiophen-3-yl 4-(dimethylamino)phenyl 3.76^([a]) 421 541 Et O O 3-chloropyridin-4-yl 1-(4-chlorophenyl)ethyl 3.78^([a]) 391 542 Et O O 1-methyl-4-(trifluoromethyl)- 1-(4-chlorophenyl)ethyl 4.2^([a]) 426 1H-pyrrol-3-yl 543 Et O O 2-chloropyridin-3-yl 1-(2,6- 3.39^([a]) 404 difluorophenyl)cyclopropyl 544 Et O O 2,3-dichloropyridin-4-yl 1-(4-chlorophenyl)ethyl 4.21^([a]) 425 545 Et O O 2-chloropyridin-3-yl 3-methyl-2-phenylbutyl 4.21^([a]) 398 546 Et O O 3-fluoropyridin-4-yl 1-(4-chlorophenyl)ethyl 3.48^([a]) 374 547 Et O O 1-methyl-4-(trifluoromethyl)- 1-(2,6- 1H-pyrrol-3-yl difluorophenyl)cyclopropyl 3.85^([a]) 440 548 Et O O 1-methyl-4-(trifluoromethyl)- 2-(methylsulfanyl)phenyl 3.73^([a]) 410 1H-pyrrol-3-yl 549 Et O O 3-(1-fluoroethyl)-1-methyl- 1-(2,6- 3.23^([a]) 419 1H-pyrazol-4-yl difluorophenyl)cyclopropyl 550 Et O O 3-(difluoromethyl)-1-methyl- 1-(4-isopropylphenyl)ethyl 4.2^([a]) 417 1H-pyrazol-4-yl 551 Et O O 3-(difluoromethyl)-1-methyl- 2-phenylpropan-2-yl 3.33^([a]) 389 1H-pyrazol-4-yl 552 Et O O 3-(difluoromethyl)-1-methyl- 1-(2,4-dichlorophenyl)ethyl 3.96^([a]) 443 1H-pyrazol-4-yl 553 Et O O 3-(difluoromethyl)-1-methyl- 1-(2-chlorophenyl)ethyl 3.46^([a]) 409 1H-pyrazol-4-yl 554 Et O O 3-(difluoromethyl)-1-methyl- 1-(3-chlorophenyl)ethyl 3.55^([a]) 409 1H-pyrazol-4-yl 555 Et O O 3-(difluoromethyl)-1-methyl- (4-chlorophenyl)methyl 3.31^([a]) 395 1H-pyrazol-4-yl 556 Et O O 3-(difluoromethyl)-1-methyl- 1-[4-(dimethylamino)phenyl]- 3.78^([a]) 472 1H-pyrazol-4-yl 2,2,2-trifluoroethyl 557 Et O O 3-(difluoromethyl)-1-methyl- 1-(2-methoxyphenyl)propyl 3.62^([a]) 419 1H-pyrazol-4-yl 558 Et O O 3-(difluoromethyl)-1-methyl- 1-(3-chlorophenyl)propyl 3.87^([a]) 423 1H-pyrazol-4-yl 559 Et O O 3-(difluoromethyl)-1-methyl- 1-(2,6- 3.17^([a]) 423 1H-pyrazol-4-yl difluorophenyl)cyclopropyl 560 Et O O 2-chloropyridin-3-yl 1-(phenoxymethyl)cyclopropyl 3.6^([a]) 398 561 Et O O 3-(difluoromethyl)-1-methyl- 1-(phenoxymethyl)cyclopropyl 3.37^([a]) 417 1H-pyrazol-4-yl 562 Et O O 2-chloropyridin-3-yl 1-(methylsulfanyl)propan-2-yl 2.77^([c]) I2; 2.71^([c]) I1; 2.73^([b]) I2; 2.73^([b]) I1 563 Me O O 2-chloropyridin-3-yl (2R)-1-amino-1-oxopropan-2-yl 1.47^([c]) T2; 1.26^([c]) T1; 1.18^([b]) 564 Me O O 2-chloropyridin-3-yl 1-methoxypropan-2-yl 2.16^([c]) I2; 2.1^([c]) I1; 2.13^([b]) 565 Me O O 2-chloropyridin-3-yl 2-methyl-1- (methylsulfanyl)propan-2-yl 566 Me O O 2-chloropyridin-3-yl [(4-methyl- 3.54^([c]); 3.53^([b]) phenyl)sulfanyl]propan-2-yl 567 Me O O 2-chloropyridin-3-yl [(2S)-1-(methylamino)-1- 1.5^([c]) T2; 1.37^([c]) T1; 1.43^([b]) T1; oxopropan-2-yl 1.43^([b]) T2 568 Me O O 2-chloropyridin-3-yl (2S)-1-amino-1-oxopropan-2-yl 1.39^([c]) T2; 1.2^([c]) T1; 1.32^([b]) T2; 1.32^([b]) T1 569 Me O O 2-chloropyridin-3-yl 2-amino-2-oxoethyl 1.14^([c]); 0.94^([b]) 570 Me O O 2-chloropyridin-3-yl (2S)-1-amino-3-hydroxy-1- 0.97^([c]); 0.79^([b]) oxopropan-2-yl 571 Et O O 2-chloropyridin-3-yl (2S)-3-methyl-1-(methoxy)-1- oxobutan-2-yl 572 Me O O 2-chloropyridin-3-yl (2S)-1-amino-3-methyl-1- 1.9^([c]) T2; 1.65^([c]) T1; 1.58^([b]) oxobutan-2-yl 573 Me O O 2-chloropyridin-3-yl 1-(dimethylamino)propan-2-yl 574 Me O O 2-chloropyridin-3-yl 4-methyl-1-(methoxy)-1- oxopentan-3-yl 575 Me O O 2-chloropyridin-3-yl (2S)-1-(methylsulfanyl)propan- 2.48^([c]) I1; 2.54^([c]) I2; 2.38^([b]) 2-yl 576 Me O O 2-chloropyridin-3-yl 1-(methylsulfanyl)propan-2-yl 2.54^([c]) I2; 2.48^([c]) I1; 2.38^([b]) 577 Me O O 2-chloropyridin-3-yl (2S)-1-(ethylsulfanyl)propan-2-yl 2.83^([c]) I1; 2.87^([c]) I2; 2.72^([b]) 578 Et O O 3-(difluoromethyl)-1-methyl- 1-(dimethylamino)propan-2-yl 1.13^([a]) 356 1H-pyrazol-4-yl 579 Et O O 3-(difluoromethyl)-1-methyl- 2-aminopropyl 0.84^([a]) 328 1H-pyrazol-4-yl 580 Me O O 2-chloropyridin-3-yl (2S)-3-methyl-1-(methoxy)-1- 2.8^([c]) T2; 2.61^([c]) T1; 2.56^([b]) oxobutan-2-yl 581 CH₂CF₃ O O 2-chloropyridin-3-yl (2S)-3-methyl-1-(methoxy)-1- 3.43^([c]) T2; 3.24^([c]) T1; 3.14^([b]) oxobutan-2-yl 582 Et O O 2-chloropyridin-3-yl (2S)-1-(methoxy)-1-oxobutan-2-yl 2.5^([c]) T2; 2.37^([c]) T1; 2.27^([b]) 583 Et O O 3-chloro-5-(trifluoromethyl)- 1-(dimethylamino)propan-2-yl 1.63^([a]) 405 pyridin-2-yl 584 Et O O 5-fluoro-1,3-dimethyl-1H- 1-(dimethylamino)propan-2-yl 0.96^([a]) 338 pyrazol-4-yl 585 CH₂CF₃ O O 2-chloropyridin-3-yl (2S)-1-(methylsulfanyl)propan- 3.14^([c]) I1; 3.19^([c]) I2; 2.98^([b]) 2-yl 586 Et O O 2-chloropyridin-3-yl (2S)-1-(ethylsulfanyl)propan-2-yl 3.19^([c]) I1; 3.25^([c]) I2; 3.06^([b]) 587 Me O O 3-(difluoromethyl)-1-methyl- 1-(dimethylamino)propan-2-y 0.82^([a]) 342 1H-pyrazol-4-yl 588 Et O O 4,5-dichloro-1,2-thiazol-3-yl 1-(dimethylamino)propan-2-yl 1.41^([a]) 377 589 Et O O 3-chloro-5-(trifluoro- 1-aminopropan-2-yl 1.59^([a]) 377 methyl)pyridin-2-yl 590 Et O O 3-(difluoromethyl)-1-methyl- 1-amino-1-oxopropan-2-yl 1.5^([a]) 342 1H-pyrazol-4-yl 591 Me O O 3-(difluoromethyl)-1-methyl- 1-aminopropan-2-yl 0.58^([a]) 314 1H-pyrazol-4-yl 592 Et O O 3-chloro-5-(trifluoro- 1-amino-1-oxopropan-2-yl 2.17^([a]) 391 methyl)pyridin-2-yl 593 Et O O 2-chloropyridin-3-yl (2S)-1-(methylsulfanyl)propan- 2.81^([c]) I1; 2.88^([c]); 2.84^([c]) I2; 2.71^([b]) 2-yl 594 Et O O 3-methylisoxazol-4-yl 1-(dimethylamino)propan-2-yl 0.76^([a]) 307 595 Et O O 2,6-dichloropyridin-3-yl (2S)-1-(methylsulfanyl)propan- 3.52^([c]); 3.59^([c]); 3.43^([c]) I1; 3.47^([c]) I2; 2-yl 3.45^([b]); 3.34^([b]) 596 Et O O 3-methylisoxazol-4-yl (2S)-1-amino-1-oxopropan-2-yl 1.41^([a]) 293 597 iPr O O 2-chloropyridin-3-yl (2S)-1-(methylsulfanyl)propan- 3.21^([c]) I2; 3.16^([c]) I1; 3.03^([b]) 2-yl 598 Me O O 3-(difluoromethyl)-1-methyl- 1-amino-1-oxopropan-2-yl 1.3^([a]) 328 1H-pyrazol-4-yl 599 Et O O 3-(difluoromethyl)-1-methyl- 1-(methylamino)-1-oxopropan- 1.66^([a]) 356 1H-pyrazol-4-yl 2-yl 600 Et O O 3-chloro-5-(trifluoro- 1-(methylamino)-1-oxopropan- 2.41^([a]) 405 methyl)pyridin-2-yl 2-yl 601 Me O O 3-(difluoromethyl)-1-methyl- 1-(methylamino)-1-oxopropan- 1.38^([a]) 342 1H-pyrazol-4-yl 2-yl 602 Et O O 1-methyl-3-(trifluoromethyl)- 1-(dimethylamino)propan-2-yl 1.36^([a]) 374 1H-pyrazol-4-yl 603 Et O O 5-chloro-1,3-dimethyl-1H- 2-aminopropyl 0.96^([a]) 326 pyrazol-4-yl 604 Et O O 3-bromothiophen-2-yl 1-(dimethylamino)propan-2-yl 1.24^([a]) 286 605 Et O O 5-chloro-1,3-dimethyl-1H- 1-(dimethylamino)propan-2-yl 1.13^([a]) pyrazol-4-yl 606 Et O O 5-chloro-1,3-dimethyl-1H- 1-(methylamino)-1-oxopropan- 1.7^([a]) 354 pyrazol-4-yl 2-yl 607 Et O O 5-chloro-1,3-dimethyl-1H- 1-amino-1-oxopropan-2-yl 1.58^([a]) pyrazol-4-yl 608 Et O O 3-(trifluoromethyl)thiophen- 1-(dimethylamino)propan-2-yl 1.63^([a]) 376 2-yl 609 Et O O 3-(trifluoromethyl)thiophen- 2-aminopropyl 1.42^([a]) 348 2-yl 610 Et O O 3-(trifluoromethyl)thiophen- 1-amino-1-oxopropan-2-yl 2.07^([a]) 362 2-yl 611 Et O O 3-bromothiophen-2-yl (2S)-1-amino-1-oxopropan-2-yl 1.9^([a]) 372 612 Et O O 3-bromothiophen-2-yl (2S)-1-(methylamino)-1- 2.07^([a]) 386 oxopropan-2-yl 613 Et O O 2-bromothiophen-3-yl 1-(dimethylamino)propan-2-yl 1.44^([a]) 386 614 allyl O O 2-chloropyridin-3-yl (2S)-1-(methylsulfanyl)propan- 2-yl 615 Et O O 2-chloropyridin-3-yl 4-(ethoxy)-4-oxobutan-2-yl 616 Me NH O 2-chloropyridin-3-yl 4-(methylamino)-4-oxobutan-2-yl 1.17^([c]) T1; 1.34^([c]) T2; 0.98^([b]) T1; 1.13^([b]) T2 617 Et O O 2,5-dimethylfuran-3-yl 1-ethoxypropan-2-yl 3.42^([a]) 618 Et O O 2,5-dimethylfuran-3-yl 1-[(butan-2-yloxy)carbonyl]- 3.94^([a]) cyclopropyl 619 Et O O 2,5-dimethylfuran-3-yl 2-methyl-1- 3.58^([a]) (methylsulfanyl)propan-2-yl 620 Me O O 2-chloropyridin-3-yl 1-(methoxycarbonyl)propan-2-yl 2.11^([a]) 621 Me O O 2-chloropyridin-3-yl 1-[(butan-2-yloxy)carbonyl]- 2.23^([a]) cyclopropyl 622 Me O O 2-chloropyridin-3-yl 1-(diethylamino)propan-2-yl 0.86^([a]) 623 Me O O 2-chloropyridin-3-yl 1-(ethoxycarbonyl)cyclopropyl 1.66^([a]) 624 Me O O 2-chloropyridin-3-yl 1-ethoxypropan-2-yl 2.42^([a]) 625 Me O O 2-chloropyridin-3-yl 1-ethoxybutan-2-yl 2.76^([a]) 626 Me O O 2-chloropyridin-3-yl 1-ethoxypentan-2-yl 3.15^([a]) 627 Me O O 2-chloropyridin-3-yl 1-ethoxy-3-methylbutan-2-yl 3.11^([a]) 628 Et O O 2-bromothiophen-3-yl (2S)-1-amino-1-oxopropan-2-yl 1.9^([a]) 372 629 Et O O 3-methylisoxazol-4-yl (2S)-1-(methylamino)-1- 1.57^([a]) 307 oxopropan-2-yl 630 Me O O 2-methyl-4-trifluoromethyl- 1-(dimethylamino)propan-2-yl 1.17^([a]) 377 1,3-thiazol-5-yl 631 Me O O 2-methyl-4-trifluoromethyl- 2-aminopropyl 0.94^([a]) 349 1,3-thiazol-5-yl 632 Et O O 1-methyl-3-(trifluoromethyl)- 1-aminopropan-2-yl 1.11^([a]) 346 1H-pyrazol-4-yl 633 Et O O 2-chloro-6-methylpyridin-3-yl (2S)-1-(methylsulfanyl)propan- 3.14^([c]) I2; 3.09^([c]) I1; 3.09^([b]) 2-yl 634 Me O O 2-methyl-4-trifluoromethyl- 1-amino-1-oxopropan-2-yl 1.69^([a]) 363 1,3-thiazol-5-yl 635 Et O O 1-methyl-3-(trifluoromethyl)- 1-amino-1-oxopropan-2-yl 1.78^([a]) 360 1H-pyrazol-4-yl 636 Et O O 1-methyl-3-(trifluoromethyl)- (2S)-1-(methylamino)-1- 1.95^([a]) 374 1H-pyrazol-4-yl oxopropan-2-yl 637 Et O O 2-bromothiophen-3-yl (2S)-1-(methylamino)-1- 2.05^([a]) 386 oxopropan-2-yl 638 Me O O 2-methyl-4-trifluoromethyl- 1-(methylamino)-1-oxopropan- 1.93^([a]) 377 1,3-thiazol-5-yl 2-yl 639 Et O O 3-(trifluoromethyl)thiophen- 1-(methylamino)-1-oxopropan- 2.25^([a]) 376 2-yl 2-yl 640 Et O O 2-methyl-4-trifluoromethyl- 1-(dimethylamino)propan-2-yl 1.35^([a]) 391 1,3-thiazol-5-yl 641 Et O O 2-methyl-4-trifluoromethyl- 1-amino-1-oxopropan-2-yl 1.96^([a]) 377 1,3-thiazol-5-yl 642 Et O O 2-methyl-4-trifluoromethyl- 1-(methylamino)-1-oxopropan- 2.07^([a]) 391 1,3-thiazol-5-yl 2-yl 643 Et O O 2-methyl-4-trifluoromethyl- 2-aminopropyl 1.11^([a]) 363 1,3-thiazol-5-yl 644 Et O O 3-chlorothiophen-2-yl (2S)-1-amino-1-oxopropan-2-yl 1.9^([a]) 328 645 Et O O 3-chlorothiophen-2-yl (2S)-1-(methylamino)-1- 2.08^([a]) 342 oxopropan-2-yl 646 Et O O 2-iodothiophen-3-yl 1-(methylamino)-1-oxopropan- 2.07^([a]) 434 2-yl 647 Et O O 2-iodothiophen-3-yl 1-amino-1-oxopropan-2-yl 1.91^([a]) 648 Et O O 2-methylpyridin-3-yl (2S)-1-(methylsulfanyl)propan- 2.2^([c]); 2.44^([b]) 2-yl 649 Et O O 3-bromothiophen-2-yl (2S)-1-methoxy-1-oxopropan-2-yl 2.96^([a]) 387 650 Et O O 3-bromothiophen-2-yl 3-methyl-1-(methoxy)-1- 3.67^([a]) 415 oxobutan-2-yl 651 Et O O 3-bromothiophen-2-yl (2S)-3-methyl-1-(methoxy)-1- 3.67^([a]) 415 oxobutan-2-yl 652 Et O O 3-bromothiophen-2-yl 1-amino-1-oxopropan-2-yl 1.94^([a]) 372 653 Et O O 3-(trifluoromethyl)thiophen- 1-(2-naphthylamino)-1- 4.01^([a]) 488 2-yl oxopropan-2-yl 654 Et O O 3-(trifluoromethyl)thiophen- 1-(2,6-dimethylphenoxy)propan- 4.89^([a]) 453 2-yl 2-yl 655 Et O O 3-(trifluoromethyl)thiophen- 1-methoxypropan-2-yl 3.31^([a]) 363 2-yl 656 Et O O 3-(trifluoromethyl)thiophen- 1-ethoxy-1-oxopropan-2-yl 3.44^([a]) 391 2-yl 657 Et O O 3-(trifluoromethyl)thiophen- (2S)-1-methoxy-1-oxopropan-2-yl 3.11^([a]) 377 2-yl 658 Et O O 3-(trifluoromethyl)thiophen- 3-methyl-1-methoxy-1- 3.62^([a]) 405 2-yl oxobutan-2-yl 659 Et O O 3-(trifluoromethyl)thiophen- (2S)-3-methyl-1-methoxy-1- 3.62^([a]) 405 2-yl oxobutan-2-yl 660 Et O O 3-(trifluoromethyl)thiophen- 1-amino-1-oxopropan-2-yl 2.13^([a]) 362 2-yl 661 Me O O 2-methyl-4-trifluoromethyl- 1-(2-naphthylamino)-1- 3.69^([a]) 489 1,3-thiazol-5-yl oxopropan-2-yl 662 Me O O 2-methyl-4-trifluoromethyl- 1-(2,6-dimethylphenoxy)propan- 4.34^([a]) 454 1,3-thiazol-5-yl 2-yl 663 Me O O 2-methyl-4-trifluoromethyl- 1-methoxypropan-2-yl 2.75^([a]) 364 1,3-thiazol-5-yl 664 Me O O 2-methyl-4-trifluoromethyl- 1-ethoxy-1-oxopropan-2-yl 2.96^([a]) 392 1,3-thiazol-5-yl 665 Me O O 2-methyl-4-trifluoromethyl- (2S)-1-methoxy-1-oxopropan-2-yl 2.62^([a]) 1,3-thiazol-5-yl 666 Me O O 2-methyl-4-trifluoromethyl- 3-methyl-1-methoxy-1- 3.29^([a]) 406 1,3-thiazol-5-yl oxobutan-2-yl 667 Me O O 2-methyl-4-trifluoromethyl- (2S)-3-methyl-1-methoxyl-1- 3.29^([a]) 406 1,3-thiazol-5-yl oxobutan-2-yl 668 Me O O 2-methyl-4-trifluoromethyl- 1-amino-1-oxopropan-2-yl 1.78^([a]) 363 1,3-thiazol-5-yl 669 Et O O 3-bromothiophen-2-yl 1-(2-naphthylamino)-1- 3.89^([a]) 498 oxopropan-2-yl 670 Et O O 3-bromothiophen-2-yl 1-(2,6-dimethylphenoxy)propan- 4.86^([a]) 463 2-yl 671 Et O O 3-bromothiophen-2-yl 1-methoxypropan-2-yl 3.17^([a]) 373 672 Et O O 3-bromothiophen-2-yl 1-ethoxy-1-oxopropan-2-y 3.33^([a]) 401 673 Et O O 3-(difluoromethyl)-1-methyl- (2S)-1-methoxy-1-oxopropan-2-yl 2.31^([a]) 357 1H-pyrazol-4-yl 674 Et O O 3-(difluoromethyl)-1-methyl- 3-methyl-1-methoxy-1- 2.84^([a]) 385 1H-pyrazol-4-yl oxobutan-2-yl 675 Et O O 3-(difluoromethyl)-1-methyl- (2S)-3-methyl-1-methoxyl-1- 2.84^([a]) 385 1H-pyrazol-4-yl oxobutan-2-yl 676 Et O O 2-methyl-4-trifluoromethyl- 1-(2-naphthylamino)-1- 3.99^([a]) 503 1,3-thiazol-5-yl oxopropan-2-yl 677 Et O O 2-methyl-4-trifluoromethyl- 1-(2,6-dimethylphenoxy)propan- 4.7^([a]) 468 1,3-thiazol-5-yl 2-yl 678 Et O O 2-methyl-4-trifluoromethyl- 1-methoxypropan-2-yl 3.11^([a]) 378 1,3-thiazol-5-yl 679 Et O O 2-methyl-4-trifluoromethyl- 1-ethoxy-1-oxopropan-2-yl 3.29^([a]) 406 1,3-thiazol-5-yl 680 Et O O 2-methyl-4-trifluoromethyl- (2S)-1-methoxy-1-oxopropan-2-yl 2.94^([a]) 392 1,3-thiazol-5-yl 681 Et O O 2-methyl-4-trifluoromethyl- 3-methyl-1-methoxy-1- 3.64^([a]) 420 1,3-thiazol-5-yl oxobutan-2-yl 682 Et O O 2-methyl-4-trifluoromethyl- (2S)-3-methyl-1-methoxyl-1- 3.64^([a]) 420 1,3-thiazol-5-yl oxobutan-2-yl 683 Et O O 3-(difluoromethyl)-1-methyl- 1-(2-naphthylamino)-1- 3.31^([a]) 468 1H-pyrazol-4-yl oxopropan-2-yl 684 Et O O 3-(difluoromethyl)-1-methyl- 1-(2,6-dimethylphenoxy)propan- 3.96^([a]) 433 1H-pyrazol-4-yl 2-yl 685 Et O O 3-(difluoromethyl)-1-methyl- 1-methoxypropan-2-yl 2.41^([a]) 343 1H-pyrazol-4-yl 686 Et O O 3-(difluoromethyl)-1-methyl- 1-ethoxy-1-oxopropan-2-yl 2.62^([a]) 371 1H-pyrazol-4-yl 687 Et O O 2-methoxypyridin-3-yl (2S)-1-(methylsulfanyl)propan- 2.96^([c]); 2.95^([b]) 2-yl 688 Et O O 3-(trifluoromethyl)thiophen- 1-(benzyloxy)but-3-en-2-yl 4.36^([a]) 451 2-yl 689 Et O O 3-bromothiophen-2-yl 1-(benzyloxy)but-3-en-2-yl 4.31^([a]) 461 690 Me O O 2-methyl-4-trifluoromethyl- 1-(benzyloxy)but-3-en-2-yl 3.89^([a]) 452 1,3-thiazol-5-yl 691 Et O O 3-(difluoromethyl)-1-methyl- 1-(benzyloxy)but-3-en-2-yl 3.51^([a]) 431 1H-pyrazol-4-yl 692 Et O O 2-methyl-4-trifluoromethyl- 1-(benzyloxy)but-3-en-2-yl 4.21^([a]) 466 1,3-thiazol-5-yl 693 Et O O 3-bromothiophen-2-yl 2-methyl-1-methoxy-1- 3.23^([a]) oxopropan-2-yl 694 Et O O 3-(trifluoromethyl)thiophen- 2-methyl-1-methoxy-1- 3.37^([a]) 2-yl oxopropan-2-yl 695 Me O O 2-methyl-4-trifluoromethyl- 2-methyl-1-methoxy-1- 2.9^([a]) 1,3-thiazol-5-yl oxopropan-2-yl 696 Et O O 3-(difluoromethyl)-1-methyl- 2-methyl-1-methoxy-1- 2.51^([a]) 1H-pyrazol-4-yl oxopropan-2-yl 697 Et O O 2-methyl-4-trifluoromethyl- 2-methyl-1-methoxy-1- 3.23^([a]) 1,3-thiazol-5-yl oxopropan-2-yl 698 Et O O 3,6-dichloropyridin-2-yl (2S)-1-amino-1-oxopropan-2-yl 1.97^([a]) 357 699 Et O O 3,5-dichloropyridin-2-yl (2S)-1-amino-1-oxopropan-2-yl 2.01^([a]) 700 Et O O 3-(trifluoromethyl)thiophen- 2-methyl-1- 3.8^([a]) 393 2-yl (methylsulfanyl)propan-2-yl 701 Et O O 3-bromothiophen-2-yl 2-methyl-1- 3.73^([a]) 403 (methylsulfanyl)propan-2-yl 702 Me O O 2-methyl-4-trifluoromethyl- 2-methyl-1- 3.27^([a]) 394 1,3-thiazol-5-yl (methylsulfanyl)propan-2-yl 703 Et O O 3-(difluoromethyl)-1-methyl- 2-methyl-1- 2.84^([a]) 373 1H-pyrazol-4-yl (methylsulfanyl)propan-2-yl 704 Et O O 2-methyl-4-trifluoromethyl- 2-methyl-1- 3.62^([a]) 408 1,3-thiazol-5-yl (methylsulfanyl)propan-2-yl 705 Et O O 2-(trifluoromethyl)pyridin-3-yl (2S)-1-amino-1-oxopropan-2-yl 1.91^([a]) 357 706 Et O O 2-(trifluoromethyl)pyridin-3-yl 1-(methylamino)-1-oxopropan- 2.05^([a]) 371 2-yl 707 Et O O 3-bromothiophen-2-yl 1-aminopropan-2-yl 1.1^([a]) 358 708 Et O O 2-chloropyridin-3-yl (2S)-1-amino-1-thioxopropan-2-yl 1.96^([c]) T2; 1.79^([c]) T1; 1.87^([b]) 709 Et O O 5-bromo-2-(methylsulfanyl)- (2S)-1-amino-1-oxopropan-2-yl 2.13^([a]) 414 pyrimidin-4-yl 710 Et O O 2,4-dichloro-1,3-thiazol-5-yl 3-methyl-1-methoxy-1- 3.82^([a]) 406 oxobutan-2-yl 711 Et O O 3-methoxy-1-methyl-1H- 3-methyl-1-methoxy-1- 2.71^([a]) 365 pyrazol-4-yl oxobutan-2-yl 712 Et O O 2,5-dichlorothiophen-3-yl 3-methyl-1-methoxy-1- 4.14^([a]) 405 oxobutan-2-yl 713 Et O O 1-methyl-3-(trifluoromethyl)- 3-methyl-1-methoxy-1- 3.09^([a]) 403 1H-pyrazol-4-yl oxobutan-2-yl 714 Et O O 2-bromothiophen-3-yl 1-methoxypropan-2-yl 3.21^([a]) 374 715 Et O O 2-bromothiophen-3-yl 3-methyl-1-methoxy-1- 3.48^([a]) 416 oxobutan-2-yl 716 Et O O 2-bromothiophen-3-yl (2-S)-3-methyl-1-methoxy-1- 3.71^([a]) 416 oxobutan-2-yl 717 Et O O 2-bromothiophen-3-yl 1-(2-naphthylamino)-1- 3.94^([a]) 499 oxopropan-2-yl 718 Et O O 2-bromothiophen-3-yl 1-(2,6-dimethylphenoxy)propan- 4.86^([a]) 464 2-yl 719 Et O O 3-ethenyl-1-methyl-1H- 3-methyl-1-methoxy-1- 2.94^([a]) 361 pyrazol-4-yl oxobutan-2-yl 720 Et O O 2,5-dichloropyridin-4-yl 1-(methylamino)-1-oxopropan- 2.19^([a]) 371 2-yl 721 Et O O 2,5-dichloropyridin-4-yl 1-amino-1-oxopropan-2-yl 2.64^([a]) 357 722 Et O O 3-chloropyridin-4-yl 1-amino-1-oxopropan-2-yl 1.65^([a]) 323 723 Et O O 3-chloropyridin-4-yl 1-(methylamino)-1-oxopropan- 1.78^([a]) 337 2-yl 724 Et O O 2-(difluoromethyl)pyridin-3-yl (2S)-1-(methylamino)-1- 1.62^([a]) 353 oxopropan-2-yl 725 Et O O 2-(difluoromethyl)pyridin-3-yl (2R)-1-(methylamino)-1- 1.45^([a]) 339 oxopropan-2-yl 726 Et O O 1-methyl-4-(trifluoromethyl)- 3-methyl-1-methoxy-1- 3.43^([a]) 402 1H-pyrrol-3-yl oxobutan-2-yl 727 Et O O 4-(trifluoromethyl)pyridin-3-yl 1-amino-1-oxopropan-2-yl 1.8^([a]) 728 Et O O 2-chloropyridin-3-yl 1-(ethylamino)-1-oxopropan-2-yl 2.1^([a]) 351 729 Et O O 2,3-dichloropyridin-4-yl (2S)-1-amino-1-oxopropan-2-yl 1.88^([a]) 358 730 Et O O 2,3-dichloropyridin-4-yl (2S)-1-(methylamino)-1- 2.08^([a]) 372 oxopropan-2-yl 731 Et O O 2-chloropyridin-3-yl 1-{[4-(trifluoromethyl)- 4.2^([a]) 468 benzyl]oxy}propan-2-yl 732 Et O O 2-chloropyridin-3-yl 1-amino-3-methyl-1-oxobutan- 2.07^([a]) 351 2-yl 733 Et O O 3-fluoropyridin-4-yl (2S)-1-amino-1-oxopropan-2-yl 1.37^([a]) 307 734 Et O O 3-bromothiophen-2-yl 1-methoxy-propan-2-yl 3.21^([a]) 373 735 Et O O 3-(difluoromethyl)-1-methyl- 1-(4-methylphenoxy)propan-2-yl 3.71^([a]) 419 1H-pyrazol-4-yl 736 Et O O 3-(difluoromethyl)-1-methyl- 1-(4-fluorophenoxy)propan-2-yl 3.42^([a]) 423 1H-pyrazol-4-yl 737 Et O O 3-(difluoromethyl)-1-methyl- 3-(phenylsulfanyl)butan-2-yl 3.87^([a]) 435 1H-pyrazol-4-yl 738 Et O O 3-(difluoromethyl)-1-methyl- 1-phenoxypropan-2-yl 3.37^([a]) 405 1H-pyrazol-4-yl 739 Et O O 3-(difluoromethyl)-1-methyl- 1-(benzyloxy)propan-2-yl 3.48^([a]) 419 1H-pyrazol-4-yl 740 Et O O 3-(difluoromethyl)-1-methyl- 1-[(2-fluorobenzyl)oxy]propan- 3.48^([a]) 437 1H-pyrazol-4-yl 2-yl 741 Et O O 3-(difluoromethyl)-1-methyl- 1-(2-chlorophenoxy)propan-2-yl 3.6^([a]) 439 1H-pyrazol-4-yl 742 Et O O 3-(difluoromethyl)-1-methyl- 1-(3-methoxyphenoxy)propan-2-yl 3.35^([a]) 435 1H-pyrazol-4-yl 743 Et O O 2-chloropyridin-3-yl (2S)-1-chloropropan-2-yl 2.72^([c]) I1; 2.75^([c]) I2; 2.7^([b]) 744 Me O O 2-chloropyridin-3-yl 1-fluoro-2-methylpropan-2-yl 2.31^([a]) 745 Et O O 2,5-dimethylfuran-3-yl 1-fluoropropan-2-yl 2.8^([a]) 746 Me O O 2-chloropyridin-3-yl 1-fluoropropan-2-yl 2.05^([a]) 747 Et O O 2,5-dichlorothiophen-3-yl 1-fluoropropan-2-yl 3.49^([a]) 351 748 Et O O 3-methoxy-1-methyl-1H- 1-fluoropropan-2-yl 2.23^([a]) 311 pyrazol-4-yl 749 Et O O 3-ethenyl-1-methyl-1H- 1-fluoropropan-2-yl 2.25^([a]) 307 pyrazol-4-yl 750 Et O O 3-chloropyridin-4-yl 1-fluoropropan-2-yl 2.42^([a]) 312 751 Et O O 1-methyl-3-(trifluoromethyl)- 1-fluoropropan-2-yl 2.72^([a]) 349 1H-pyrazol-4-yl 752 Et O O 1-methyl-4-(trifluoromethyl)- 1-fluoropropan-2-yl 2.95^([a]) 348 1H-pyrrol-3-yl 753 Et O O 3-(difluoromethyl)-1-methyl- 2,3,3-trimethylbutan-2-yl 3.46^([a]) 369 1H-pyrazol-4-yl 754 Me O O 2-methyl-4-trifluoromethyl- 2,3,3-trimethylbutan-2-yl 4.02^([a]) 1,3-thiazol-5-yl 755 Et O O 3-bromothiophen-2-yl 2,3,3-trimethylbutan-2-yl 4.67^([a]) 399 756 Me O O 2-chloropyridin-3-yl pentan-3-yl 2.76^([a]) 757 Me O O 2-chloropyridin-3-yl 4,4,4-trifluorobutan-2-yl 2.34^([a]) 758 Me O O 2-chloropyridin-3-yl 4,4,4-trifluoro-2-methylbutan-2-yl 2.34^([a]) 759 Me O O 2-chloropyridin-3-yl 2-fluorocyclopropyl 1.87^([a]) 760 Et O O 2-chloropyridin-3-yl 1-(cyclohex-3-en-1-yl)ethyl 3.9^([a]) 761 Et O O 2-chloropyridin-3-yl cyclohexyl 3.55^([a]) 762 Me O O 2-chloropyridin-3-yl 1-cyclohexylpropyl 4.07^([a]) 763 Me O O 2-chloropyridin-3-yl cyclopentyl 2.61^([a]) 764 Et O O 2-chloropyridin-3-yl cyclopropyl 2.5^([c]); 2.36^([b]) 765 Me O O 2-chloropyridin-3-yl dicyclopropylmethyl 2.85^([a]) 766 Me O O 2-chloropyridin-3-yl 1-cyclopropylpropan-2-yl 2.84^([a]) 767 Et O O 2-chloropyridin-3-yl (2S)-1-bromopropan-2-yl 2.83^([c]) I1; 2.87^([c]) I2; 2.79^([b]) 768 Me O O 2-chloropyridin-3-yl 1-(1-chlorocyclopropyl)ethyl 2.72^([a]) 769 Et O O 3-(trifluoromethyl)thiophen- 1-(1-chlorocyclopropyl)ethyl 4.04^([a]) 393 2-yl 770 Me O O 2-methyl-4-trifluoromethyl- 1-(1-chlorocyclopropyl)ethyl 3.53^([a]) 394 1,3-thiazol-5-yl 771 Et O O 3-bromothiophen-2-yl 1-(1-chlorocyclopropyl)ethyl 3.94^([a]) 403 772 Et O O 2-methyl-4-trifluoromethyl- 1-(1-chlorocyclopropyl)ethyl 3.89^([a]) 408 1,3-thiazol-5-yl 773 Et O O 3-(difluoromethyl)-1-methyl- 1-(1-chlorocyclopropyl)ethyl 373 1H-pyrazol-4-yl 774 Et O O 2-bromothiophen-3-yl 1-(1-chlorocyclopropyl)ethyl 3.92^([a]) 404 775 Me O O 2-chloropyridin-3-yl tBu 2.31^([a]) 776 Et O O 5-bromo-2-(methyl- tBu 3.82^([a]) 401 sulfanyl)pyrimidin-4-yl 777 Et O O 5-bromo-2-(methyl- tBu 3.06^([a]) sulfanyl)pyrimidin-4-yl 778 Et O O 2-chloropyridin-3-yl 4-methylpentan-2-yl 3.76^([c]) I2; 3.72^([c]) I1; 3.62^([b]) 779 Et O O 2,5-dimethylfuran-3-yl 4-methylpentan-2-yl 4.35^([a]) 780 Et O O 3-(difluoromethyl)-1-methyl- 4-methylpentan-2-yl 3.46^([a]) 355 1H-pyrazol-4-yl 781 Et O O 3-(trifluoromethyl)thiophen- 4-methylpentan-2-yl 4.54^([a]) 375 2-yl 782 Me O O 2-methyl-4-trifluoromethyl- 4-methylpentan-2-yl 3.9^([a]) 376 1,3-thiazol-5-yl 783 Et O O 3-bromothiophen-2-yl 4-methylpentan-2-yl 4.46^([a]) 385 784 Et O O 2-methyl-4-trifluoromethyl- 4-methylpentan-2-yl 4.29^([a]) 390 1,3-thiazol-5-yl 785 Et O O 2-bromothiophen-3-yl 4-methylpentan-2-yl 4.41^([a]) 386 786 Et O O 3-(trifluoromethyl)thiophen- cyanomethyl 2-yl 787 Me O O 2-methyl-4-trifluoromethyl- cyanomethyl 2.01^([a]) 331 1,3-thiazol-5-yl 788 Et O O 3-(difluoromethyl)-1-methyl- cyanomethyl 1.79^([a]) 310 1H-pyrazol-4-yl 789 Et O O 3-bromothiophen-2-yl cyanomethyl 2.33^([a]) 340 790 Et O O 2-methyl-4-trifluoromethyl- cyanomethyl 2.35^([a]) 345 1,3-thiazol-5-yl 791 Et O O 2-bromothiophen-3-yl cyanomethyl 2.32^([a]) 341 792 Et O O 2-chloropyridin-3-yl (2S)-1-cyanopropan-2-yl 2.22^([c]); 2.09^([c]) I1; 2.17^([c]) I2; 2.13^([b]) 793 Me O O 2-chloropyridin-3-yl cyclobutyl 2.34^([a]) 794 Et O O 3,6-dichloropyridin-2-yl cBu 3.58^([a]) 340 795 Et O O 3,5-dichloropyridin-2-yl cBu 3.67^([a]) 340 796 Et O O 4,6-dichloropyridin-3-yl cBu 3.55^([a]) 797 Et O O 2,5-dichloropyridin-4-yl cBu 3.55^([a]) 340 798 Et O O 3-chloropyridin-4-yl cBu 2.84^([a]) 306 799 Et O O 2-(difluoromethyl)pyridin-3-yl cBu 2.76^([a]) 322 800 Et O O 4-(trifluoromethyl)pyridin-3-yl cBu 3.06^([a]) 340 801 Et O O 4,6-dichloropyridin-2-yl cBu 3.79^([a]) 802 Et O O 2,3-dichloropyridin-4-yl cBu 3.52^([a]) 341 803 Et O O 3-bromopyridin-4-yl cBu 2.9^([a]) 350 804 Et O O 3-fluoropyridin-4-yl cBu 2.66^([a]) 290 805 Et O O 3-(trifluoromethyl)pyridin-4-yl cBu 3.6^([a]) 340 806 Et O O 2-chloropyridin-3-yl F₃iPr 3.1^([c]) I2; 2.99^([c]) I1; 2.9^([b]) 807 Et O O 2-methoxypyridin-3-yl F₃iPr 3.05^([c]); 3.04^([b]) 808 Et O O 3-methoxy-1-methyl-1H- F₃iPr 2.82^([a]) 347 pyrazol-4-yl 809 Et O O 2,4-dichloro-1,3-thiazol-5-yl F₃iPr 3.75^([a]) 388 810 Et O O 2,5-dichlorothiophen-3-yl F₃iPr 4.11^([a]) 387 811 Et O O 1-methyl-3-(trifluoromethyl)- F₃iPr 3.29^([a]) 285 1H-pyrazol-4-yl 812 Et O O 1-methyl-4-(trifluoromethyl)- F₃iPr 3.64^([a]) 384 1H-pyrrol-3-yl 813 Et O O 5-fluoro-1,3-dimethyl-1H- octan-2-yl 4.51^([a]) 365 pyrazol-4-yl 814 Et O O 3-bromothiophen-2-yl octan-2-yl 5.48^([a]) 413 815 Et O O 3-(trifluoromethyl)thiophen- octan-2-yl 5.48^([a]) 403 2-yl 816 Me O O 2-methyl-4-trifluoromethyl- octan-2-yl 4.86^([a]) 404 1,3-thiazol-5-yl 817 Et O O 3-(difluoromethyl)-1-methyl- octan-2-yl 4.36^([a]) 383 1H-pyrazol-4-yl 818 Et O O 2-methyl-4-trifluoromethyl- octan-2-yl 5.22^([a]) 418 1,3-thiazol-5-yl 819 Et O O 2-chloropyridin-3-yl octan-2-yl 4.53^([c]); 4.55^([b]) 820 Et O O 2-bromothiophen-3-yl octan-2-yl 5.41^([a]) 414 821 Et O O 2-chloropyridin-3-yl (2S)-hexan-2-yl 3.69^([c]) I1; 3.71^([c]) I2 822 Me O O 2-chloropyridin-3-yl iPr 2.11^([a]) 823 Et O O 2-chloropyridin-3-yl iPr 2.66^([a]); 2.54^([c]); 2.53^([b]) 824 Et O O 2-chloropyridin-3-yl sBu 825 Et O O 2,5-dimethylfuran-3-yl (2S)-butan-2-yl 3.63^([a]) 826 Me O O 2-chloropyridin-3-yl (2S)-butan-2-yl 2.55^([a]) 827 Et O O 3-bromothiophen-2-yl (2S)-butan-2-yl 3.76^([a]) 357 828 Et O O 3-bromothiophen-2-yl (2R)-butan-2-yl 3.76^([a]) 357 829 Et O O 3-(trifluoromethyl)thiophen- (2R)-butan-2-yl 3.83^([a]) 347 2-yl 830 Et O O 3-(trifluoromethyl)thiophen- (2S)-butan-2-yl 3.83^([a]) 347 2-yl 831 Me O O 2-methyl-4-trifluoromethyl- (2S)-butan-2-yl 3.23^([a]) 348 1,3-thiazol-5-yl 832 Me O O 2-methyl-4-trifluoromethyl- (2R)-butan-2-yl 3.23^([a]) 348 1,3-thiazol-5-yl 833 Et O O 3-(difluoromethyl)-1-methyl- (2R)-butan-2-yl 2.82^([a]) 327 1H-pyrazol-4-yl 834 Et O O 3-(difluoromethyl)-1-methyl- (2S)-butan-2-yl 2.82^([a]) 327 1H-pyrazol-4-yl 835 Et O O 2-methyl-4-trifluoromethyl- (2S)-butan-2-yl 3.59^([a]) 362 1,3-thiazol-5-yl 836 Et O O 2-methyl-4-trifluoromethyl- (2R)-butan-2-yl 3.59^([a]) 362 1,3-thiazol-5-yl 837 Et O O 3,6-dichloropyridin-2-yl sBu 3.67^([a]) 342 838 Et O O 4,6-dichloropyridin-3-yl sBu 3.64^([a]) 342 839 Et O O 3,5-dichloropyridin-2-yl sBu 3.78^([a]) 342 840 Et O O 2-(trifluoromethyl)pyridin-3-yl sBu 3.27^([a]) 342 841 Et O O 5-bromo-2-(methyl- sBu 3.89^([a]) 399 sulfanyl)pyrimidin-4-yl 842 Et O O 2-(difluoromethyl)pyridin-3-yl sBu 2.87^([a]) 324 843 Et O O 4-(trifluoromethyl)pyridin-3-yl sBu 3.17^([a]) 844 Et O O 3-bromothiophen-2-yl (2R)-heptan-2-yl 5.03^([a]) 399 845 Et O O 3-bromothiophen-2-yl (2S)-heptan-2-yl 5.03^([a]) 399 846 Et O O 3-bromothiophen-2-yl heptan-2-yl 5.03^([a]) 399 847 Et O O 3-(trifluoromethyl)thiophen- (2R)-heptan-2-yl 5.05^([a]) 389 2-yl 848 Et O O 3-(trifluoromethyl)thiophen- (2S)-heptan-2-yl 5.05^([a]) 389 2-yl 849 Et O O 3-(trifluoromethyl)thiophen- heptan-2-yl 5.05^([a]) 389 2-yl 850 Me O O 2-methyl-4-trifluoromethyl- (2R)-heptan-2-yl 4.41^([a]) 390 1,3-thiazol-5-yl 851 Me O O 2-methyl-4-trifluoromethyl- (2S)-heptan-2-yl 4.41^([a]) 390 1,3-thiazol-5-yl 852 Me O O 2-methyl-4-trifluoromethyl- heptan-2-yl 4.41^([a]) 390 1,3-thiazol-5-yl 853 Et O O 3-(difluoromethyl)-1-methyl- (2S)-heptan-2-yl 3.94^([a]) 369 1H-pyrazol-4-yl 854 Et O O 3-(difluoromethyl)-1-methyl- (2R)-heptan-2-yl 3.94^([a]) 369 1H-pyrazol-4-yl 855 Et O O 3-(difluoromethyl)-1-methyl- heptan-2-yl 3.94^([a]) 369 1H-pyrazol-4-yl 856 Et O O 2-methyl-4-trifluoromethyl- (2S)-heptan-2-yl 4.81^([a]) 404 1,3-thiazol-5-yl 857 Et O O 2-methyl-4-trifluoromethyl- (2R)-heptan-2-yl 4.81^([a]) 404 1,3-thiazol-5-yl 858 Et O O 2-methyl-4-trifluoromethyl- heptan-2-yl 4.81^([a]) 404 1,3-thiazol-5-yl 859 Et O O 2-chloropyridin-3-yl heptan-2-yl 4.1^([c]) I1; 4.12^([c]) I2; 4.1^([b]) 860 Et O O 2-bromothiophen-3-yl (2R)-heptan-2-yl 4.94^([a]) 861 Et O O 2-bromothiophen-3-yl (2S)-heptan-2-yl 4.94^([a]) 400 862 Et O O 2-bromothiophen-3-yl heptan-2-yl 4.99^([a]) 400 863 Et O O 2-chloropyridin-3-yl pentan-2-yl 864 Et O O 3-(difluoromethyl)-1-methyl- pentan-2-yl 3.19^([a]) 341 1H-pyrazol-4-yl 865 Et O O 3-(trifluoromethyl)thiophen- pentan-2-yl 4.21^([a]) 361 2-yl 866 Me O O 2-methyl-4-trifluoromethyl- pentan-2-yl 3.61^([a]) 362 1,3-thiazol-5-yl 867 Et O O 3-bromothiophen-2-yl pentan-2-yl 4.16^([a]) 371 868 Et O O 2-methyl-4-trifluoromethyl- pentan-2-yl 3.96^([a]) 376 1,3-thiazol-5-yl 869 Me O O 2-chloropyridin-3-yl 1-cyanoethyl 1.85^([c]); 1.86^([b]) 870 Me O O 2-chloropyridin-3-yl (1S)-1-cyclohexylethyl 3.9^([c]) I2; 3.87^([c]) I1; 3.76^([b]) 871 Me O O 2-chloropyridin-3-yl (1R)-1-cyclohexylethyl 3.9^([c]) I2; 3.87^([c]) I1; 3.76^([b]) 872 Et O O 3-(difluoromethyl)-1-methyl- 1-cyclohexylethyl 3.92^([a]) 381 1H-pyrazol-4-yl 873 Et O O 3-(trifluoromethyl)thiophen- 1-cyclohexylethyl 5.11^([a]) 401 2-yl 874 Me O O 2-methyl-4-trifluoromethyl- 1-cyclohexylethyl 4.46^([a]) 402 1,3-thiazol-5-yl 875 Et O O 3-bromothiophen-2-yl 1-cyclohexylethyl 5.11^([a]) 411 876 Et O O 2-methyl-4-trifluoromethyl- 1-cyclohexylethyl 4.86^([a]) 416 1,3-thiazol-5-yl 877 Et O O 2-bromothiophen-3-yl 1-cyclohexylethyl 5.03^([a]) 412 878 Et O O 2-chloropyridin-3-yl 1-cyclopropylethyl 3.1^([c]) I2; 3.05^([c]) I1; 2.93^([b]) 879 Et O O 2,5-dimethylfuran-3-yl 1-cyclopropylethyl 3.63^([a]) 880 Me O O 2-chloropyridin-3-yl 1-cyclopropylethyl 2.58^([a]) 881 Et O O 2-chloro-6-methylpyridin-3-yl 1-cyclopropylethyl 3.32^([c]) I1; 3.37^([c]) I2; 3.32^([b]) 882 Et O O 3-(difluoromethyl)-1-methyl- 1-cyclopropylethyl 2.88^([a]) 339 1H-pyrazol-4-yl 883 Et O O 3-(trifluoromethyl)thiophen- 1-cyclopropylethyl 3.83^([a]) 359 2-yl 884 Me O O 2-methyl-4-trifluoromethyl- 1-cyclopropylethyl 3.27^([a]) 360 1,3-thiazol-5-yl 885 Et O O 3-bromothiophen-2-yl 1-cyclopropylethyl 3.76^([a]) 369 886 Et O O 2-methyl-4-trifluoromethyl- 1-cyclopropylethyl 3.61^([a]) 374 1,3-thiazol-5-yl 887 Et O O 2,5-dichlorothiophen-3-yl 1-cyclopropylethyl 4.36^([a]) 359 888 Et O O 3,6-dichloropyridin-2-yl 1-cyclopropylethyl 3.73^([a]) 354 889 Et O O 3,5-dichloropyridin-2-yl 1-cyclopropylethyl 3.8^([a]) 354 890 Et O O 4,6-dichloropyridin-3-yl 1-cyclopropylethyl 3.64^([a]) 891 Et O O 3-methoxy-1-methyl-1H- 1-cyclopropylethyl 2.8^([a]) 319 pyrazol-4-yl 892 Et O O 2-(trifluoromethyl)pyridin-3-yl 1-cyclopropylethyl 3.35^([a]) 354 893 Et O O 2,4-dichloro-1,3-thiazol-5-yl 1-cyclopropylethyl 3.87^([a]) 360 894 Et O O 1-methyl-3-(trifluoromethyl)- 1-cyclopropylethyl 3.29^([a]) 357 1H-pyrazol-4-yl 895 Et O O 3-(1-fluoroethyl)-1-methyl- 1-cyclopropylethyl 2.84^([a]) 335 1H-pyrazol-4-yl 896 Et O O 2,5-dichloropyridin-4-yl 1-cyclopropylethyl 3.69^([a]) 354 897 Et O O 4-(trifluoromethyl)pyridin-3-yl 1-cyclopropylethyl 3.2^([a]) 354 898 Et O O 3-chloropyridin-4-yl 1-cyclopropylethyl 3.03^([a]) 320 899 Et O O 2-(difluoromethyl)pyridin-3-yl 1-cyclopropylethyl 2.9^([a]) 336 900 Et O O 4,6-dichloropyridin-2-yl 1-cyclopropylethyl 3.92^([a]) 901 Et O O 1-methyl-4-(trifluoromethyl)- 1-cyclopropylethyl 3.56^([a]) 356 1H-pyrrol-3-yl 902 Et O O 2,3-dichloropyridin-4-yl 1-cyclopropylethyl 3.61^([a]) 355 903 Et O O 3-bromopyridin-4-yl 1-cyclopropylethyl 3^([a]) 364 904 Et O O 3-fluoropyridin-4-yl 1-cyclopropylethyl 2.8^([a]) 304 905 Et O O 3-(trifluoromethyl)pyridin-4-yl 1-cyclopropylethyl 3.2^([a]) 354 906 allyl O O 2-chloropyridin-3-yl 1-cyclopropylethyl 3.06^([c]) I1; 3.11^([c]) I2; 3.08^([b]) 907 Et NH O 2-chloropyridin-3-yl 1-cyclopropylethyl 2.54^([c]) I1; 2.59^([c]) I2; 2.53^([b]) I1; 2.58^([b]) I2 908 Me NH O 2-chloropyridin-3-yl 1-cyclopropylethyl 2.2^([c]); 2.2^([b]) 909 Et O O 2-chloropyridin-3-yl (1S)-1-cyclopropylethyl 3.1^([a]) 910 Et O O 2-chloropyridin-3-yl (1R)-1-cyclopropylethyl 3.1^([a]) 911 Me NOMe O 2-chloropyridin-3-yl 1-cyclopropylethyl 2.4^([c]); 2.41^([b]) 912 H N(NHC O 2-chloropyridin-3-yl 1-cyclopropylethyl 1.53^([c]); 1.5^([b]) OMe) 913 Et O O 2-chloropyridin-3-yl (1S)-1-cyclopropylethyl 2.9^([c]) I1; 2.96^([c]) I2; 2.9^([b]) 914 Et O O 2,6-dichloropyridin-3-yl (1S)-1-cyclopropylethyl 3.59^([c]) I2; 3.54^([c]) I1; 3.54^([b]) 915 allyl O O 2-chloropyridin-3-yl (1S)-1-cyclopropylethyl 3.11^([c]) I2; 3.06^([c]) I1; 3.08^([b]) 916 Me O O 2-chloropyridin-3-yl (2S)-3,3-dimethylbutan-2-yl 3.28^([c]) I2; 3.24^([c]) I1; 3.14^([b]) 917 Me O O 2-chloropyridin-3-yl (2S)-3,3-dimethylbutan-2-yl 3.28^([c]) I2; 3.24^([c]) I1; 3.14^([b]) 918 Et O O 3-(difluoromethyl)-1-methyl- 3,3-dimethylbutan-2-yl 3.37^([a]) 355 1H-pyrazol-4-yl 919 Et O O 3-(trifluoromethyl)thiophen- 3,3-dimethylbutan-2-yl 4.46^([a]) 375 2-yl 920 Me O O 2-methyl-4-trifluoromethyl- 3,3-dimethylbutan-2-yl 3.83^([a]) 376 1,3-thiazol-5-yl 921 Et O O 3-bromothiophen-2-yl 3,3-dimethylbutan-2-yl 4.41^([a]) 385 922 Et O O 2-methyl-4-trifluoromethyl- 3,3-dimethylbutan-2-yl 4.21^([a]) 390 1,3-thiazol-5-yl 923 Et O O 2-bromothiophen-3-yl 3,3-dimethylbutan-2-yl 4.36^([a]) 386 924 Et O O 2-chloropyridin-3-yl (2S)-3,3-dimethylbutan-2-yl 3.6^([a]) 925 Et O O 3-(difluoromethyl)-1-methyl- 6-methylheptan-2-yl 4.26^([a]) 383 1H-pyrazol-4-yl 926 Et O O 3-(trifluoromethyl)thiophen- 6-methylheptan-2-yl 5.39^([a]) 403 2-yl 927 Me O O 2-methyl-4-trifluoromethyl- 6-methylheptan-2-yl 4.78^([a]) 404 1,3-thiazol-5-yl 928 Et O O 3-bromothiophen-2-yl 6-methylheptan-2-yl 5.36^([a]) 413 929 Et O O 2-methyl-4-trifluoromethyl- 6-methylheptan-2-yl 5.14^([a]) 418 1,3-thiazol-5-yl 930 Et O O 2-bromothiophen-3-yl 6-methylheptan-2-yl 5.32^([a]) 414 931 Me O O 2-chloropyridin-3-yl 3-methylbutan-2-yl 2.76^([a]); 3^([c]); 2.83^([b]) 932 Me O O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.99^([c]) I2; 2.96^([c]) I1; 2.85^([b]) 933 Et O O 3-(difluoromethyl)-1-methyl- 3-methylbutan-2-yl 3.13^([a]) 341 1H-pyrazol-4-yl 934 Et O O 2-chloropyridin-3-yl 3-methylbutan-2-yl 3.36^([c]) I2; 3.33^([c]) I1; 3.21^([b]) 935 Et O O 3-chloro-5-(trifluoro- 3-methylbutan-2-yl 4.29^([a)] 390 methyl)pyridin-2-yl 936 Et O O 5-fluoro-1,3-dimethyl-1H- 3-methylbutan-2-yl 3.19^([a]) 323 pyrazol-4-yl 937 Et O O 4,5-dichloro-1,2-thiazol-3-yl 3-methylbutan-2-yl 4.39^([a]) 362 938 Me O O 3-(difluoromethyl)-1-methyl- 3-methylbutan-2-yl 2.8^([a]) 327 1H-pyrazol-4-yl 939 Et O O 1-methyl-3-(trifluoromethyl)- 3-methylbutan-2-yl 3.64^([a]) 359 1H-pyrazol-4-yl 940 Et O O 3-methylisoxazol-4-yl 3-methylbutan-2-yl 3.15^([a]) 292 941 Et O O 3-bromothiophen-2-yl 3-methylbutan-2-yl 4.12^([a]) 371 942 Me O O 2-bromopyridin-3-yl (2S)-3-methylbutan-2-yl 3.02^([c]); 2.88^([b]) 943 Et O O 5-chloro-1,3-dimethyl-1H- 3-methylbutan-2-yl 3.67^([a]) 339 pyrazol-4-yl 944 Et O O 3-(trifluoromethyl)thiophen- 3-methylbutan-2-yl 4.21^([a]) 361 2-yl 945 Et O O 2-bromothiophen-3-yl 3-methylbutan-2-yl 4.1^([a]) 371 946 iPr O O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.73^([c]) I2; 3.7^([c]) I1; 3.69^([b]) 947 Et O O 2,5-dimethylfuran-3-yl 3-methylbutan-2-yl 3.99^([a]) 948 Me O O 2-methyl-4-trifluoromethyl- 3-methylbutan-2-yl 3.63^([a]) 362 1,3-thiazol-5-yl 949 Et O O 2-methyl-4-trifluoromethyl- 3-methylbutan-2-yl 3.95^([a]) 376 1,3-thiazol-5-yl 950 Et O O 2-chloro-6-methylpyridin-3-yl (2S)-3-methylbutan-2-yl 3.64^([c]) I1; 3.67^([c]) I2; 3.63^([b]) 951 Et O O 3-chlorothiophen-2-yl 3-methylbutan-2-yl 4.08^([a]) 327 952 Et O O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.37^([a]); 3.34^([c]) I1; 3.36^([c]) I2; 3.33^([b]) 953 Et O O 2-methylpyridin-3-yl (2S)-3-methylbutan-2-yl 2.63^([c]); 2.89^([b]) 954 Et O O 5-chloro-3-(difluoromethyl)- 3-methylbutan-2-yl 3.63^([a]) 375 1-methyl-1H-pyrazol-4-yl 955 allyl O O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.55^([a]); 3.53^([c]) I2; 3.5^([c]) I1; 3.49^([b]) 956 H O O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.2^([a]) 957 iPr NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.37^([c]); 3.39^([b]) 958 Et NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.94^([a]); 2.95[c]; 2.82^([c]); 2.95^([b]); 2.82^([b]) 959 Me NMe O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 960 OMe NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.31^([c]); 2.26^([b]) 961 Et O O 2-methoxypyridin-3-yl (2S)-3-methylbutan-2-yl 3.52^([c]); 3.52^([b]) 962 allyl O O 3-bromothiophen-2-yl 3-methylbutan-2-yl 4.34^([a]) 383 963 Et O O 2-hydroxypyridin-3-yl (2S)-3-methylbutan-2-yl 964 H O O 3-bromothiophen-2-yl 3-methylbutan-2-yl 2.74^([a]) 343 965 Et O O 2,5-dichlorothiophen-3-yl 3-methylbutan-2-yl 4.72^([a]) 361 966 Et O O 3,6-dichloropyridin-2-yl 3-methylbutan-2-yl 4.06^([a]) 356 967 Et O O 3,5-dichloropyridin-2-yl 3-methylbutan-2-yl 4.19^([a]) 356 968 Et O O 4,6-dichloropyridin-3-yl 3-methylbutan-2-yl 3.96^([a]) 356 969 Et O O 3-methoxy-1-methyl-1H- 3-methylbutan-2-yl 3.06^([a]) 321 pyrazol-4-yl 970 Et O O 2-(trifluoromethyl)pyridin-3-yl 3-methylbutan-2-yl 3.62^([a]) 356 971 Et O O 3-ethenyl-1-methyl-1H- 3-methylbutan-2-yl 3.06^([a]) 317 pyrazol-4-yl 972 Et O O 5-bromo-2-(methyl- 3-methylbutan-2-yl 4.26^([a]) sulfanyl)pyrimidin-4-yl 973 Et O O 2,4-dichloro-1,3-thiazol-5-yl 3-methylbutan-2-yl 4.23^([a]) 362 974 Et O O 2-(4-chlorophenyl)pyridin-3-yl (2S)-3-methylbutan-2-yl 4.09^([c]); 4.08^([b]) 975 Et O O 2-(3,5-dichlorophenyl)- (2S)-3-methylbutan-2-yl 4.68^([c]); 4.67^([b]) pyridin-3-yl 976 Et O O 2-ethenylpyridin-3-yl (2S)-3-methylbutan-2-yl 3.24^([c]); 3.26^([b]) 977 Et O O 2,5-dichloropyridin-4-yl 3-methylbutan-2-yl 3.96^([a]) 356 978 Et O O 3-chloropyridin-4-yl 3-methylbutan-2-yl 3.29^([a]) 322 979 Et O O 2-(1-ethoxyethenyl)pyridin- (2S)-3-methylbutan-2-yl 3-yl 980 Et O O 2-acetylpyridin-3-yl (2S)-3-methylbutan-2-yl 3.11^([c]); 3.08^([b]) 981 Et O O 2-(difluoromethyl)pyridin-3-yl 3-methylbutan-2-yl 3.15^([a]) 338 982 Et O O 4-(trifluoromethyl)pyridin-3-yl 3-methylbutan-2-yl 3.5^([a]) 356 983 Et O O 4,6-dichloropyridin-2-yl 3-methylbutan-2-yl 4.26^([a]) 984 Et O O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.33^([a]); 3.22^([c]); 3.22^([b]) 985 Et O O 2-(N-hydroxyethan- (2S)-3-methylbutan-2-yl 2.69^([c]); 2.67^([b]) imidoyl)pyridin-3-yl 986 Et O O 2,6-dichloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.85^([c]); 3.85^([b]) 987 Et O O 1-methyl-4-(trifluoromethyl)- 3-methylbutan-2-yl 3.84^([a]) 358 1H-pyrrol-3-yl 988 nPr NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.24^([c]); 3.22^([b]) 989 Me NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.41^([c]); 2.41^([b]) 990 1H-benzo- O O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.22^([c]); 3.21^([b]) triazol- 1-yl 991 propargyl NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.69^([c]); 2.68^([b]) 992 CH₂CF₃ NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.17^([c]); 3.16^([b]) 993 H NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 1.97^([c]); 1.96^([b]) 994 Et O O 2,3-dichloropyridin-4-yl (2S)-3-methylbutan-2-yl 3.92^([a]) 357 996 Et O O 3-bromopyridin-4-yl (2S)-3-methylbutan-2-yl 3.33^([a]) 366 997 Et O O 3-fluoropyridin-4-yl (2S)-3-methylbutan-2-yl 3.08^([a]) 306 998 allyl O O 3-(difluoromethyl)-1-methyl- (2S)-3-methylbutan-2-yl 3.31^([a]) 353 1H-pyrazol-4-yl 999 Et O O 5-fluoro-1-methyl-3-(trifluo- (2S)-3-methylbutan-2-yl 3.93^([a]) 377 romethyl)-1H-pyrazol-4-yl 1000 Et O O 3-(difluoromethyl)-5-fluoro- 3-methylbutan-2-yl 3.53^([a]) 359 1-methyl-1H-pyrazol-4-yl 1001 Et O O 5-chloro-1-methyl-3-(trifluo- 3-methylbutan-2-yl 4.06^([a]) 393 romethyl)-1H-pyrazol-4-yl 1002 Et O O 3-(1,1-difluoroethyl)-1- 3-methylbutan-2-yl 3.39^([a]) 355 methyl-1H-pyrazol-4-yl 1003 Et O O 3-(difluoromethyl)-1-methyl- (2S)-3-methylbutan-2-yl 3.15^([a]) 341 1H-pyrazol-4-yl 1004 CH₂CF₃ NH O 3-(difluoromethyl)-1-methyl- (2S)-3-methylbutan-2-yl 392* 1H-pyrazol-4-yl 1005 2-MeOEt NH O 3-(difluoromethyl)-1-methyl- (2S)-3-methylbutan-2-yl 2.59^([a]) 370 1H-pyrazol-4-yl 1006 cPr NH O 3-(difluoromethyl)-1-methyl- (2S)-3-methylbutan-2-yl 2.66^([a]) 352 1H-pyrazol-4-yl 1007 allyl NH O 3-(difluoromethyl)-1-methyl- (2S)-3-methylbutan-2-yl 2.9^([a]) 352 1H-pyrazol-4-yl 1008 allyl NH O 3-(difluoromethyl)-1-methyl- (2S)-3-methylbutan-2-yl 2.68^([a]) 350 1H-pyrazol-4-yl 1009 Me O O 2-chloropyridin-3-yl 1-methylcyclohexyl 3.13^([a]) 1010 Me O O 2-methyl-4-trifluoromethyl- 2-cyanopropan-2-yl 3.04^([a]) 358 1,3-thiazol-5-yl 1011 Et O O 3,6-dichloropyridin-2-yl 2-cyanopropan-2-yl 2.98^([a]) 353 1012 Et O O 2-chloropyridin-3-yl allyl 1013 Et O O 5-chloro-1,3-dimethyl-1H- octa-1,7-dien-3-yl 4.04^([a]) 377 pyrazol-4-yl 1014 Et O O 3-(trifluoromethyl)thiophen- octa-1,7-dien-3-yl 4.7^([a]) 399 2-yl 1015 Et O O 3-chloro-5-(trifluoromethyl)- octa-1,7-dien-3-yl 4.82^([a]) 428 pyridin-2-yl 1016 Et O O 3-(difluoromethyl)-1-methyl- octa-1,7-dien-3-yl 3.73^([a]) 379 1H-pyrazol-4-yl 1017 Et O O 3-bromothiophen-2-yl octa-1,7-dien-3-yl 4.67^([a]) 409 1018 Et O O 2-bromothiophen-3-yl octa-1,7-dien-3-yl 4.67^([a]) 409 1019 Me O O 2-methyl-4-trifluoromethyl- octa-1,7-dien-3-yl 4.19^([a]) 400 1,3-thiazol-5-yl 1020 Et O O 3-methylisoxazol-4-yl octa-1,7-dien-3-yl 3.81^([a]) 330 1021 Et O O 1-methyl-3-(trifluoromethyl)- octa-1,7-dien-3-yl 4.14^([a]) 397 1H-pyrazol-4-yl 1022 Et O O 2-methyl-4-trifluoromethyl- octa-1,7-dien-3-yl 4.49^([a]) 414 1,3-thiazol-5-yl 1023 Et O O 3-chlorothiophen-2-yl octa-1,7-dien-3-yl 4.65^([a]) 365 1024 Et O O 2-iodothiophen-3-yl octa-1,7-dien-3-yl 4.65^([a]) 457 1025 Me O O 2-chloropyridin-3-yl 2-methylhex-3-yn-2-yl 2.98^([a]) 1026 Et O O 3-(difluoromethyl)-1-methyl- 2-methylbut-3-yn-2-yl 2.53^([a]) 338 1H-pyrazol-4-yl 1027 Et O O 3-bromothiophen-2-yl 2-methylbut-3-yn-2-yl 3.42^([a]) 367 1028 Me O O 2-chloropyridin-3-yl 2-methylbut-3-yn-2-yl 2.23^([a]) 1029 Et O O 2-bromothiophen-3-yl 2-methylbut-3-yn-2-yl 3.42^([a]) 367 1030 Et O O 3-methylisoxazol-4-yl 2-methylbut-3-yn-2-yl 2.66^([a]) 288 1031 Et O O 1-methyl-3-(trifluoromethyl)- 2-methylbut-3-yn-2-yl 3.02^([a]) 355 1H-pyrazol-4-yl 1032 Et O O 3-chlorothiophen-2-yl 2-methylbut-3-yn-2-yl 3.41^([a]) 323 1033 Et O O 2,5-dichlorothiophen-3-yl 2-methylbut-3-yn-2-yl 3.99^([a]) 357 1034 Et O O 3-methoxy-1-methyl-1H- 2-methylbut-3-yn-2-yl 2.44^([a]) 317 pyrazol-4-yl 1035 Et O O 3-ethenyl-1-methyl-1H- 2-methylbut-3-yn-2-yl 2.54^([a]) 313 pyrazol-4-yl 1036 Et O O 2,4-dichloro-1,3-thiazol-5-yl 2-methylbut-3-yn-2-yl 3.61^([a]) 358 1037 Et O O 2,3-dichloropyridin-4-yl 2-methylbut-3-yn-2-yl 1038 Et O O 1-methyl-4-(trifluoromethyl)- 2-methylbut-3-yn-2-yl 3.21^([a]) 1H-pyrrol-3-yl 1039 Me O O 2-chloropyridin-3-yl 2-methylpent-3-yn-2-yl 2.57^([a]) 1040 Et O O 3-(trifluoromethyl)thiophen- 2-methylpent-3-yn-2-yl 3.92^([a]) 371 2-yl 1041 Et O O 3-bromothiophen-2-yl 2-methylpent-3-yn-2-yl 3.85^([a]) 381 1042 Me O O 2-methyl-4-trifluoromethyl- 2-methylpent-3-yn-2-yl 3.35^([a]) 372 1,3-thiazol-5-yl 1043 Et O O 3-(difluoromethyl)-1-methyl- 2-methylpent-3-yn-2-yl 2.9^([a]) 351 1H-pyrazol-4-yl 1044 Et O O 2-chloropyridin-3-yl prop-2-yn-1-yl 2.18^([c]); 2.05^([b]) 1045 Me O O 2-chloropyridin-3-yl but-3-yn-2-yl 2.14^([a]) 1046 Et O O 3-(trifluoromethyl)thiophen- but-3-yn-2-yl 3.25^([a]) 343 2-yl 1047 Et O O 3-bromothiophen-2-yl but-3-yn-2-yl 3.17^([a]) 353 1048 Me O O 2-methyl-4-trifluoromethyl- but-3-yn-2-yl 2.73^([a]) 344 1,3-thiazol-5-yl 1049 Et O O 3-(difluoromethyl)-1-methyl- but-3-yn-2-yl 2.44^([a]) 323 1H-pyrazol-4-yl 1050 Et O O 2-methyl-4-trifluoromethyl- but-3-yn-2-yl 3.06^([a]) 358 1,3-thiazol-5-yl 1051 Me O O 2-chloropyridin-3-yl pent-3-yn-2-yl 2.5^([a]) 1052 Et O O 2-chloropyridin-3-yl pent-3-yn-2-yl 2.86^([a]) 318 1053 Et O O 2-chloropyridin-3-yl 3-(methylsulfanyl)cyclohexyl 3.57^([c]) I1; 3.68^([c]) I2; 3.54^([b]); 3.43^([b]) I1 1054 Et O O 2-chloropyridin-3-yl 2-(trifluoromethyl)cyclopropyl 2.9^([a]) 360 1055 Et O O 2-chloropyridin-3-yl 2,2-dimethylcyclopropyl 3.25^([a]) 1056 Me O O 2-chloropyridin-3-yl 2,4-dimethylcyclohexyl 3.73^([a]) 1057 Me O O 2-chloropyridin-3-yl 2,5-dimethylcyclohexyl 3.73^([a]) 1058 Me O O 2-chloropyridin-3-yl 2,6-dimethylcyclohexyl 3.63^([a]) 1059 Me O O 2-chloropyridin-3-yl 2-ethoxycyclopentyl 2.93^([a]) 1060 Me O O 2-chloropyridin-3-yl 2-ethyl-6-methylcyclohexyl 3.99^([a]) 1061 Me O O 2-chloropyridin-3-yl 2-ethylcyclohexyl 3.63^([a]) 1062 Et O O 2-chloropyridin-3-yl 2-ethylcyclopropyl 3.27^([a]) 320 1063 Me O O 2-chloropyridin-3-yl 2-ethylnylcyclohexyl 2.99^([a]) 1064 Et O O 2-chloropyridin-3-yl 2-hydroxycyclohexyl 2.03^([c]) T1; 2.33^([c]) T2; 2.27^([b]) 1065 Et O O 2-chloropyridin-3-yl 2-methylcyclobutyl 3.37^([a]) 1066 Et O O 2-chloropyridin-3-yl 2-methylcyclohexyl 3.84^([c]); 3.7^([b]) 1067 Et O O 2-chloropyridin-3-yl 2-methylcyclopropyl 2.86^([a]) 306 1068 Et O O 2-chloropyridin-3-yl 2-phenylcyclopropyl 3.44^([a]) 368 1069 Me O O 2-chloropyridin-3-yl 3-(trifluoromethyl)cyclohexyl 3.09^([a]) 1070 Me O O 2-chloropyridin-3-yl 3,4-dimethylcyclohexyl 3.73^([a]) 1071 Me O O 2-chloropyridin-3-yl 3,5-bis(trifluoromethyl)- 3.42^([a]) cyclohexyl 1072 Et O O 2-bromothiophen-3-yl 3-ethyl-3,5,5-trimethyl- 454 cyclohexyl 1073 Et O O 2-chloropyridin-3-yl 3-methylcyclobutyl 3.3^([a]) 1074 Me O O 2-chloropyridin-3-yl 3-methylcyclohexyl 3.37^([a]) 1075 Me O O 2-chloropyridin-3-yl 4-(trifluoromethyl)cyclohexyl 3.04^([a]) 1076 Me O O 2-chloropyridin-3-yl 4-methylcyclohexyl 3.37^([a]) 1077 Me O O 2-chloropyridin-3-yl 4-tert-butylcyclohexyl 4.51^([a]) 1078 Me O O 2-chloropyridin-3-yl 2,3-dihydro-1H-inden-1-yl 3.06^([a]) 1079 Et O O 3-(difluoromethyl)-1-methyl- 2,3-dihydro-1H-indene-1-yl 3.42^([a]) 387 1H-pyrazol-4-yl 1080 Et O O 2-chloropyridin-3-yl bicyclo[2.2.1]hept-2-yl 3.59^([c]); 3.57^([b]) 1081 Et O O 2-chloropyridin-3-yl (1S,4R)-bicyclo[2.2.1]hept-2-yl 3.7^([a]) 346 1082 Et O O 2-chloropyridin-3-yl (1R,4S)-bicyclo[2.2.1]hept-2-yl 3.74^([a]) 1083 Et O O 2-chloropyridin-3-yl bicyclo[4.1.0]hept-7-yl 3.73^([a]) 346 1084 Me O O 2-chloropyridin-3-yl decahydronaphthalen-1-yl 4.25^([a]) 1085 Et O O 2-chloropyridin-3-yl (trimethylsilyl)methyl 3.59^([c]); 3.46^([b]) 1086 Et O O 3-bromothiophen-2-yl 2-ethoxy-2-oxo-1-phenylethyl 1087 Et O O 2-chloropyridin-3-yl 2-(methylamino)-2-oxo-1- 2.43^([a]) 399 phenylethyl 1088 Me O O 2-chloropyridin-3-yl 1-ethynylcyclohexyl 2.99^([a]) 1089 Et O O 3-bromothiophen-2-yl 4-(4-cyanophenyl)-2-methylbut- 4.16^([a]) 468 3-yn-2-yl 1090 Et O O 3-(difluoromethyl)-1-methyl- 4-(4-cyanophenyl)-2-methylbut- 3.37^([a]) 438 1H-pyrazol-4-yl 3-yn-2-yl 1091 Et O O 3-(trifluoromethyl)thiophen- 4-(4-cyanophenyl)-2-methylbut- 4.24^([a]) 458 2-yl 3-yn-2-yl 1092 Me O O 2-methyl-4-trifluoromethyl- 4-(4-cyanophenyl)-2-methylbut- 3.78^([a]) 459 1,3-thiazol-5-yl 3-yn-2-yl 1093 Et O O 2-methyl-4-trifluoromethyl- 4-(4-cyanophenyl)-2-methylbut- 4.04^([a]) 473 1,3-thiazol-5-yl 3-yn-2-yl 1094 Et O O 2-bromothiophen-3-yl 4-(4-cyanophenyl)-2-methylbut- 4.21^([a]) 469 3-yn-2-yl 1095 Me O O 2-methyl-4-trifluoromethyl- 2-methyl-4-(4- 4.51^([a]) 448 1,3-thiazol-5-yl methylphenyl)but-3-yn-2-yl 1096 Et O O 3-bromothiophen-2-yl 2-methyl-4-(4- 5.05^([a]) 457 methylphenyl)but-3-yn-2-yl 1097 Et O O 3-(difluoromethyl)-1-methyl- 2-methyl-4-(4- 4.11^([a]) 427 1H-pyrazol-4-yl methylphenyl)but-3-yn-2-yl 1098 Et O O 2-methyl-4-trifluoromethyl- 2-methyl-4-(4- 4.92^([a]) 462 1,3-thiazol-5-yl methylphenyl)but-3-yn-2-yl 1099 Et O O 3-(trifluoromethyl)thiophen- 5-methoxy-2-methylpent-3-yn- 3.55^([a]) 401 2-yl 2-yl 1100 Me O O 2-methyl-4-trifluoromethyl- 5-methoxy-2-methylpent-3-yn- 3.06^([a]) 402 1,3-thiazol-5-yl 2-yl 1101 Et O O 3-(difluoromethyl)-1-methyl- 5-methoxy-2-methylpent-3-yn- 2.73^([a]) 381 1H-pyrazol-4-yl 2-yl 1102 Et O O 2-methyl-4-trifluoromethyl- 5-methoxy-2-methylpent-3-yn- 3.42^([a]) 416 1,3-thiazol-5-yl 2-yl 1103 Et O O 3-(trifluoromethyl)thiophen- 4,4-dichloro-2-methylbut-3-en- 4.26^([a]) 427 2-yl 2-yl 1104 Me O O 2-methyl-4-trifluoromethyl- 4,4-dichloro-2-methylbut-3-en- 3.73^([a]) 428 1,3-thiazol-5-yl 2-yl 1105 Et O O 3-bromothiophen-2-yl 4,4-dichloro-2-methylbut-3-en- 4.21^([a]) 437 2-yl 1106 Et O O 3-(difluoromethyl)-1-methyl- 4,4-dichloro-2-methylbut-3-en- 3.31^([a]) 1H-pyrazol-4-yl 2-yl 1107 Et O O 2-chloropyridin-3-yl (2S)-1-[(methyl- 2.28^([c]) T2; 2.12^([c]) T1; 2.17^([b]) sulfonyl)oxy]propan-2-yl 1108 Et O O 2-chloropyridin-3-yl 1-(methylsulfonyl)propan-2-yl 1.69^([c]) I1; 1.77^([c]) I2; 1.86^([c]); 1.8^([b]) I2; 1.8^([b]); 1.77^([b]) I1 1109 Et O O 2-chloropyridin-3-yl (2S)-1-thiocyanatopropan-2-yl 2.44^([c]) T2; 2.32^([c]) T1; 2.35^([b]) 1111 Et O O 2-chloropyridin-3-yl 1-{[(1-phenylethylidene)amino]- 3.96^([a]) 427 oxy}propan-2-yl 1112 Et O O 3-(difluoromethyl)-1- 1-{[(1-phenylethylidene)amino]- 3.83^([a]) 446 methyl-1H-pyrazol-4-yl oxy}propan-2-yl 1113 Me O O 2-chloropyridin-3-yl 1-(trifluoromethyl)cyclohexyl 2.99^([a]) 1114 Et NH O 2-chloropyridin-3-yl (1S)-1-cyclopropylethyl 2.54^([c]) I1; 2.59^([c]) I2; 2.58^([b]) I2; 2.53^([b]) I1 1115 cPr NH O 2-chloropyridin-3-yl 1-cyclopropylethyl 2.54^([c]) I2; 2.48^([c]) I1; 2.47^([b]) I1; 2.53^([b]) I2 1116 OMe NH O 2-chloropyridin-3-yl (1S)-1-cyclopropylethyl 1117 Et O O 2-chloropyridin-3-yl 1-(5,6-dihydro-1,4,2-dioxazin-3- 2.11^([a]) 365 yl)ethyl 1118 Et NH O 2-chloropyridin-3-yl 1-(pyrimidin-4-yl)ethyl 1.62^([a]) 357 1119 Et NH O 2-chloropyridin-3-yl pent-3-yn-2-yl 2.5^([a]) 317 1120 Et NH O 2-chloropyridin-3-yl 2-(1,3-thiazol-2-yl)propyl 2.14^([a]) 376 1121 Et O O 2-cyanopyridin-3-yl (2S)-3-methylbutan-2-yl 313 1122 Et O O 3-(difluoromethyl)-1-methyl- 2-methylcyclohexyl 3.6^([a]) 367 1H-pyrazol-4-yl 1123 Et O O 3-(difluoromethyl)-1-methyl- cBu 2.73^([a]) 325 1H-pyrazol-4-yl 1124 Et O O 3-(difluoromethyl)-1-methyl- cPr 2.35^([a]) 311 1H-pyrazol-4-yl 1125 Et O O 3-(difluoromethyl)-1-methyl- (2S)-hexan-2-yl 3.58^([a]) 355 1H-pyrazol-4-yl 1126 Et O O 3-(difluoromethyl)-1-methyl- (trimethylsilyl)methyl 3.35^([a]) 357 1H-pyrazol-4-yl 1127 Et O O 3-(difluoromethyl)-1-methyl- allyl 2.35^([a]) 311 1H-pyrazol-4-yl 1128 Et O O 3-(difluoromethyl)-1-methyl- propargyl 2.13^([a]) 309 1H-pyrazol-4-yl 1129 Et O O 3-(difluoromethyl)-1-methyl- 1-ethoxy-4-methyl-1-oxopentan- 3.53^([a]) 413 1H-pyrazol-4-yl 2-yl 1130 Et O O 3-(difluoromethyl)-1-methyl- 2-methylcyclopropyl 2.68^([a]) 325 1H-pyrazol-4-yl 1131 Et O O 3-(difluoromethyl)-1-methyl- bicyclo[4.1.0]hept-7-yl 3.44^([a]) 365 1H-pyrazol-4-yl 1132 Et O O 3-(difluoromethyl)-1-methyl- 1-cyanocyclopropyl 2.1^([a]) 336 1H-pyrazol-4-yl 1133 Et O O 3-(difluoromethyl)-1-methyl- 1-cyclobutylethyl 3.33^([a]) 353 1H-pyrazol-4-yl 1134 Et O O 3-(difluoromethyl)-1-methyl- 1-(bicyclo[2.2.1]hept-2-yl)ethyl 4.03^([a]) 393 1H-pyrazol-4-yl 1135 Et O O 3-(difluoromethyl)-1-methyl- 1-(2,2-dimethylpropoxy)propan- 4.08^([a]) 399 1H-pyrazol-4-yl 2-yl 1136 Et O O 3-(difluoromethyl)-1-methyl- 1-cyclopropylpropan-2-yl 3.23^([a]) 353 1H-pyrazol-4-yl 1137 Et O O 3-(difluoromethyl)-1-methyl- 2-(methylamino)-2-oxo-1- 2.27^([a]) 418 1H-pyrazol-4-yl phenylethyl 1138 Et O O 3-(difluoromethyl)-1-methyl- 4-[(2-methylphenyl)amino]-4- 2.68^([a]) 446 1H-pyrazol-4-yl oxobutan-2-yl 1139 Et O O 3-(difluoromethyl)-1-methyl- 4-ethoxy-4-oxobutan-2-yl 2.66^([a]) 385 1H-pyrazol-4-yl 1140 Et O O 3-(difluoromethyl)-1-methyl- 2-methoxy-2-oxo-1-phenylethyl 2.94^([a]) 419 1H-pyrazol-4-yl 1141 Et O O 3-(difluoromethyl)-1-methyl- 1-(cyclohex-3-en-1-yl)ethyl 3.62^([a]) 379 1H-pyrazol-4-yl 1142 Et O O 3-(difluoromethyl)-1-methyl- pent-3-yn-2-yl 2.8^([a]) 337 1H-pyrazol-4-yl 1143 Et O O 3-(difluoromethyl)-1-methyl- 1-(prop-1-yn-1-yl)cyclopentyl 3.39^([a]) 377 1H-pyrazol-4-yl 1144 Et O O 3-(difluoromethyl)-1-methyl- (1R,2R,4S)-bicyclo[2.2.1]hept- 3.46^([a]) 365 1H-pyrazol-4-yl 2-yl 1145 Et O O 3-(difluoromethyl)-1-methyl- (1S,4R)-bicyclo[2.2.1]hept-2-yl 3.42^([a]) 365 1H-pyrazol-4-yl 1146 Et O O 3-(difluoromethyl)-1-methyl- 2-ethylcyclopropyl 3.04^([a]) 339 1H-pyrazol-4-yl 1147 Et O O 3-(difluoromethyl)-1-methyl- 2-(trifluoromethyl)cyclopropyl 2.75^([a]) 379 1H-pyrazol-4-yl 1148 Et O O 3-(difluoromethyl)-1-methyl- 2,2-dimethylcyclopropyl 3^([a]) 339 1H-pyrazol-4-yl 1149 Et O O 2-chloropyridin-3-yl 1-(4-fluorophenyl)ethyl 3.51^([a]) 374 1150 Et O O 2-chloropyridin-3-yl 1-(4-methylphenyl)ethyl 3.87^([a]) 370 1151 Et O O 2-chloropyridin-3-yl 1-phenylethyl 3.48^([a]) 356 1152 Et O O 2-chloropyridin-3-yl 1-(3-chlorophenyl)ethyl 3.83^([a]) 390 1153 Et O O 2-chloropyridin-3-yl 4-methoxyphenyl 2.98^([a]) 358 1154 Et O O 2-chloropyridin-3-yl 4-(propan-2-yl)phenyl 4.08^([a]) 370 1155 Et O O 2-chloropyridin-3-yl 1-(2-methylphenoxy)propan-2-yl 4.01^([a]) 400 1156 Et O O 2-chloropyridin-3-yl 1-[(4-chlorophenyl)sulfanyl]- 4.08^([a]) 436 propan-2-yl 1157 Et O O 2-chloropyridin-3-yl 1-[(2,5-dichlorophenyl)- 4.27^([a]) 470 sulfanyl]propan-2-yl 1158 Et O O 2-chloropyridin-3-yl 1-[(3,4-dichlorophenyl)- 4.41^([a]) 470 sulfanyl]propan-2-yl 1159 Et O O 2-chloropyridin-3-yl 3-(phenylsulfanyl)butan-2-yl 4.13^([a]) 416 1160 Et O O 2-chloropyridin-3-yl 1-[3-(trifluoromethyl)- 4.13^([a]) 454 phenoxy]propan-2-yl 1161 Et O O 2-chloropyridin-3-yl 1-phenoxypropan-2-yl 3.58^([a]) 386 1162 Et O O 2-chloropyridin-3-yl 1-(benzyloxy)propan-2-yl 3.71^([a]) 400 1163 Et O O 2-chloropyridin-3-yl 1-[(2-fluorobenzyl)oxy]propan- 3.69^([a]) 418 2-yl 1164 Et O O 2-chloropyridin-3-yl 1-(2-chlorophenoxy)propan-2-yl 3.78^([a]) 420 1165 Et O O 2-chloropyridin-3-yl 1-(4-methylphenoxy)propan-2-yl 3.94^([a]) 400 1166 Et O O 2-chloropyridin-3-yl 1-(4-fluorophenoxy)propan-2-yl 3.62^([a]) 404 1167 Et O O 2-chloropyridin-3-yl 4-phenylbutan-2-yl 3.92^([a]) 384 1168 Et O O 2-chloropyridin-3-yl 2-(propan-2-yloxy)phenyl 3.8^([a]) 386 1169 Et O O 2-chloropyridin-3-yl 4-(difluoromethoxy)phenyl 3.19^([a]) 394 1170 Et O O 2-chloropyridin-3-yl 4-(methylsulfanyl)phenyl 3.37^([a]) 374 1171 Et O O 2-chloropyridin-3-yl 2-(methylsulfanyl)benzyl 3.37^([a]) 388 1172 Et O O 2-chloropyridin-3-yl 1-[(2-chlorobenzyl)oxy]propan- 4.06^([a]) 434 2-yl 1173 Et O O 2-chloropyridin-3-yl 1-(3-methoxyphenoxy)propan-2-yl 3.58^([a]) 416 1174 Et O O 2-chloropyridin-3-yl (2R)-butan-2-yl 3^([a]) 308 1175 Et O O 2-chloropyridin-3-yl pentyl 3.53^([a]) 322 1176 Et O O 2-chloropyridin-3-yl octa-1,7-dien-3-yl 4.01^([a]) 360 1177 Et O O 2-chloropyridin-3-yl 1-(bicyclo[2.2.1]hept-2-yl)ethyl 4.39^([a]) 374 1178 Et O O 2-chloropyridin-3-yl 1-(2,2-dimethylpropoxy)propan- 4.34^([a]) 380 2-yl 1179 Et O O 2-chloropyridin-3-yl 1-cyclopropylpropan-yl 3.42^([a]) 334 1180 Et O O 2-chloropyridin-3-yl 1-(2,6-dimethylphenoxy)propan- 4.26^([a]) 414 2-yl 1181 Et O O 2-chloropyridin-3-yl but-3-yn-2-yl 2.66^([a]) 304 1182 Et O O 2-chloropyridin-3-yl 1-(1-chlorocyclopropyl)ethyl 3.33^([a]) 354 1183 Et O O 2-chloropyridin-3-yl 2-MeOEt 2.17^([a]) 310 1184 Et O O 2-chloropyridin-3-yl 4-hydroxybutyl 1.75^([a]) 324 1185 Et O O 2-chloropyridin-3-yl 3-methylbutyl 3.44^([a]) 322 1186 Et O O 2-chloropyridin-3-yl cBu 2.92^([a]) 306 1187 Et O O 2-chloropyridin-3-yl 6-methylheptan-2-yl 4.62^([a]) 364 1188 Et O O 2-chloropyridin-3-yl (2R)-heptan-2-yl 4.26^([a]) 350 1189 Et O O 2-chloropyridin-3-yl (2S)-heptan-2-yl 4.26^([a]) 350 1190 Et O O 2-chloropyridin-3-yl 2-ethylcyclopropyl 3.23^([a]) 320 1191 Et O O 2-chloropyridin-3-yl 1-cyclobutylethyl 3.55^([a]) 334 1192 Et O O 2-chloropyridin-3-yl 4-[(2-methylphenyl)amino]-4- 2.8^([a]) 427 oxobutan-2-yl 1193 Et O O 2-chloropyridin-3-yl 1-(naphthalen-2-ylamino)-1- 3.51^([a]) 449 oxopropan-2-yl 1194 Et O O 2-chloropyridin-3-yl 1-ethoxy-1-oxopropan-2-yl 2.82^([a]) 352 1195 Et O O 2-chloropyridin-3-yl 2-methoxy-2-oxo-1-phenylethyl 3.08^([a]) 400 1196 Et O O 2-chloropyridin-3-yl 1-ethoxy-4-methyl-1-oxopentan- 3.89^([a]) 394 2-yl 1197 Et O O 2-chloropyridin-3-yl 1-(benzyloxy)but-3-en-2-yl 3.8^([a]) 412 1198 Et O O 2-chloropyridin-3-yl pent-3-yn-2-yl 3.02^([a]) 318 1199 Et NH O 2-cyanopyridin-3-yl (2S)-3-methylbutan-2-yl 2.64^([a]) 1200 Et NH O 2,3-dichloropyridin-4-yl (2S)-3-methylbutan-2-yl 3.57^([a]) 356 1201 Et NH O 2,3-dichloropyridin-4-yl 1-(pyridin-2-yl)ethyl 2.53^([a]) 391 1202 Et O O 3-iodo-1-methyl-1H- 3-methylbutan-2-yl 3.22^([a]) 417 pyrazol-4-yl 1203 Et O O 1,3-dimethyl-1H-pyrazol-4-yl 3-methylbutan-2-yl 2.8^([a]) 305 1204 Et O O 1,3-dimethyl-1H-pyrazol-4-yl 1-(pyridin-2-yl)ethyl 1.99^([a]) 340 1205 Et O O 3-ethyl-1-methyl-1H- 3-methylbutan-2-yl 3.13^([a]) 319 pyrazol-4-yl 1206 Et O O 3-ethyl-1-methyl-1H- 1-(pyridin-2-yl)ethyl 2.25^([a]) 354 pyrazol-4-yl 1207 Et O O 1-methyl-3-(propan-2-yl)- 1-(pyridin-2-yl)ethyl 2.58^([a]) 368 1H-pyrazol-4-yl 1208 Et O O 1-methyl-3-(propan-2-yl)- 3-methylbutan-2-yl 3.46^([a]) 333 1H-pyrazol-4-yl 1209 Et O O 2-bromo-3-chloropyridin-4-yl (2S)-3-methylbutan-2-yl 3.94^([a]) 401 1210 Et NH O 2-bromo-3-chloropyridin-4-yl (2S)-3-methylbutan-2-yl 3.6^([a]) 400 1211 Et O O 3-chloro-2-methylpyridin-4-yl (2S)-3-methylbutan-2-yl 3.51^([a]) 336 1212 Et O O 1,3-dimethyl-1H-pyrazol-4-yl 1-(1,3-thiazol-2-yl)ethyl 2.11^([a]) 346 1213 Et O O 3-ethyl-1-methyl-1H- 1-(1,3-thiazol-2-yl)ethyl 2.35^([a]) 360 pyrazol-4-yl 1214 Et O O 1-methyl-3-(propan-2-yl)- 1-(1,3-thiazol-2-yl)ethyl 2.62^([a]) 374 1H-pyrazol-4-yl 1215 Et O O 3-(difluoromethyl)-1- 2-(4-chlorophenyl)propan-2-yl 3.71^([a]) 423 methyl-1H-pyrazol-4-yl 1216 Et O O 3-(difluoromethyl)-1- 2-chlorophenyl 3.15^([a]) 381 methyl-1H-pyrazol-4-yl 1217 Et O O 3-(difluoromethyl)-1- 4-cyanophenyl 2.64^([a]) 372 methyl-1H-pyrazol-4-yl 1218 Et O O 3-(difluoromethyl)-1- (2-bromophenyl)(cyano)methyl 3.13^([a]) 464 methyl-1H-pyrazol-4-yl 1219 Et O O 3-(difluoromethyl)-1- cyano(2,3- 3.44^([a]) 454 methyl-1H-pyrazol-4-yl dichlorophenyl)methyl 1220 Et O O 3-(difluoromethyl)-1- 1-cyanobut-3-yn-1-yl 2.33^([a]) 348 methyl-1H-pyrazol-4-yl 1221 Et O O 3-(difluoromethyl)-1- 1-cyano-2-phenylethyl 2.98^([a]) 400 methyl-1H-pyrazol-4-yl 1222 Et O O 3-(difluoromethyl)-1- 1-(4-chlorophenyl)-2,2,2- 4.01^([a]) 463 methyl-1H-pyrazol-4-yl trifluoroethyl 1223 Et O O 3-(difluoromethyl)-1- 1,1,1-trifluoro-3-(3-methyl- 2.94^([a]) 458 methyl-1H-pyrazol-4-yl pyridin-2-yl)propan-2-yl 1224 Et O O 3-(difluoromethyl)-1- 2,2,2-trifluoro-1-phenylethyl 3.55^([a]) 429 methyl-1H-pyrazol-4-yl 1225 Et O O 3-(difluoromethyl)-1- 1-(3-methoxyphenyl)ethyl 3.21^([a]) 405 methyl-1H-pyrazol-4-yl 1226 Et O O 3-(difluoromethyl)-1- 2-(cyclopropylcarbonyl)phenyl 3^([a]) 415 methyl-1H-pyrazol-4-yl 1227 Et O O 3-(difluoromethyl)-1- 2-(trifluoromethoxy)phenyl 3.42^([a]) 431 methyl-1H-pyrazol-4-yl 1228 Et O O 3-(difluoromethyl)-1- 2-(ethylsulfanyl)phenyl 3.46^([a]) 407 methyl-1H-pyrazol-4-yl 1229 Et O O 3-(difluoromethyl)-1- 2-(4-methoxyphenyl)propan-2-yl 3.35^([a]) 419 methyl-1H-pyrazol-4-yl 1230 Et O O 3-(difluoromethyl)-1- cyano(phenyl)methyl 2.94^([a]) 386 methyl-1H-pyrazol-4-yl 1231 Et O O 3-(difluoromethyl)-1- cyano(2,4- 3.55^([a]) 454 methyl-1H-pyrazol-4-yl dichlorophenyl)methyl 1232 Et O O 3-(difluoromethyl)-1- cyano(1-phenyl-1H-pyrazol-4- 3.15^([a]) 452 methyl-1H-pyrazol-4-yl yl)methyl 1233 Et O O 3-(difluoromethyl)-1- 1-{[4-(trifluoromethyl)benzyl[- 3.99^([a]) 487 methyl-1H-pyrazol-4-yl oxy}propan-2-yl 1234 Et O O 3-(difluoromethyl)1-methyl 1-[(4-chlorophenyl)sulfanyl]- 3.87^([a]) 455 1H-pyrazol-4-yl propan-2-yl 1235 Et O O 3-(difluoromethyl)-1-methyl- 1-[(2,5-dichlorophenyl)- 4.08^([a]) 489 1H-pyrazol-4-yl sulfanyl]propan-2-yl 1236 Et O O 3-(difluoromethyl)-1-methyl- 1-[(3,4-dichlorophenyl)- 4.2^([a]) 489 1H-pyrazol-4-yl sulfanyl]propan-2-yl 1237 Et O O 3-(difluoromethyl)-1-methyl- 1-[3-(trifluoromethyl)- 3.92^([a]) 473 1H-pyrazol-4-yl phenoxy]propan-2-yl 1238 Et O O 3-(difluoromethyl)-1-methyl- 4-(4-cyanophenyl)-2-methylbut- 3.69^([a]) 438 1H-pyrazol-4-yl 3-yn-2-yl 1239 Et O O 3-(difluoromethyl)-1-methyl- 3-methyl-2-phenylbutyl 3.94^([a]) 417 1H-pyrazol-4-yl 1240 Et O O 3-(difluoromethyl)-1-methyl- 3-oxopentan-2-yl 2.47^([a]) 355 1H-pyrazol-4-yl 1241 Et O O 3-(difluoromethyl)-1-methyl- 1-[(2-chlorobenzyl)oxy]propan- 3.83^([a]) 453 1H-pyrazol-4-yl 2-yl 1242 Et O O 3-(difluoromethyl)-1-methyl- 1-(2-methylphenoxy)propan-2-yl 3.78^([a]) 419 1H-pyrazol-4-yl 1243 Et O O 3-chloro-2-methylpyridin-4-yl 1-(pyridin-2-yl)ethyl 2.6^([a]) 371 1244 Me NH O 2-chloropyridin-3-yl (1S)-1-cyclopropylethyl 2.16^([c]) I1; 2.21^([c]) I2; 2.16^([b)] I1; 2.2^([b]) I2 1245 cBu O O 2-chloropyridin-3-yl (1S)-1-cyclopropylethyl 3.43^([c]) I1; 3.5^([c]) I2; 3.46^([b]) 1246 OMe NMe O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.68^([c]); 2.67^([b]) 1247 Et O O 3-iodo-1-methyl-1H- 1-(1,3-thiazol-2-yl)ethyl 3.46^([a]) 458 pyrazol-4-yl 1248 Et O O 3-iodo-1-methyl-1H- 1-(pyridin-2-yl)ethyl 2.37^([a]) 452 pyrazol-4-yl 1249 Et NH O 3-chloro-2-methylpyridin-4-yl (2S)-3-methylbutan-2-yl 3.08^([a]) 335 1250 Et O O 3-(difluoromethyl)-1-methyl- 1-cyanobutyl 2.77^([a]) 352 1H-pyrazol-4-yl 1251 Et O O 3-(difluoromethyl)-1-methyl- 1-cyanopropyl 2.45^([a]) 338 1H-pyrazol-4-yl 1252 Et O O 3-(difluoromethyl)-1-methyl- 1-cyano-3-methylbutyl 3.04^([a]) 366 1H-pyrazol-4-yl 1253 Et O O 3-(difluoromethyl)-1-methyl- F₃iPr 2.92^([a]) 367 1H-pyrazol-4-yl 1254 Et O O 3-(difluoromethyl)-1-methyl- 1-cyanoethyl 2.15^([a]) 324 1H-pyrazol-4-yl 1255 Et O O 3-(difluoromethyl)-1-methyl- 2-amino-2-oxoethyl 2.1^([a]) 328 1H-pyrazol-4-yl 1256 Et O O 3-(difluoromethyl)-1-methyl- 1-(ethylamino)-1-oxopropan-2-yl 1.88^([a]) 370 1H-pyrazol-4-yl 1257 Et O O 2-chloropyridin-3-yl cyano(2,3-dichlorophenyl)- 3.69^([a]) 435 methyl 1258 Et O O 2-chloropyridin-3-yl 1-cyanobut-3-yn-1-yl 2.37^([a]) 329 1259 Et O O 2-chloropyridin-3-yl 1-cyano-2-phenylethyl 3.02^([a]) 381 1260 Et O O 2-chloropyridin-3-yl 1-[4-(dimethylamino)phenyl]- 3.99^([a]) 453 2,2,2-trifluoroethyl 1261 Et O O 2-chloropyridin-3-yl 1-(4-chlorophenyl)-2,2,2- 4.25^([a]) 444 trifluoroethyl 1262 Et O O 2-chloropyridin-3-yl 1,1,1-trifluoro-3-(3- 3.04^([a]) 439 methylpyridin-2-yl)propan-2-yl 1263 Et O O 2-chloropyridin-3-yl 2-chlorophenyl 3.35^([a]) 362 1264 Et O O 2-chloropyridin-3-yl 4-(dimethylamino)phenyl 3.17^([a]) 371 1265 Et O O 2-chloropyridin-3-yl 4-cyanophenyl 2.73^([a]) 353 1266 Et O O 2-chloropyridin-3-yl 3-(methylsulfanyl)phenyl 3.42^([a]) 374 1267 Et O O 2-chloropyridin-3-yl cyano(2,4- 3.83^([a]) 435 dichlorophenyl)methyl 1268 Et O O 2-chloropyridin-3-yl 2-methyl-4-(4- 4.41^([a]) 408 methylphenyl)but-3-yn-2-yl 1269 Et O O 2-chloropyridin-3-yl 1,3-benzothiazol-6-yl 2.54^([a]) 385 1270 Et O O 2-chloropyridin-3-yl 3-oxopentan-2-yl 2.64^([a]) 336 1271 Et O O 2-chloropyridin-3-yl 4,4-dichloro-2-methylbut-3-en- 3.55^([a]) 388 2-yl 1272 Et O O 2-chloropyridin-3-yl 4-(4-cyanophenyl)-2-methylbut- 3.67^([a]) 419 3-yn-2-yl 1273 Et O O 2-chloropyridin-3-yl 2,3,3-trimethylbutan-2-yl 3.8^([a]) 350 1274 Et O O 2-chloropyridin-3-yl 1-methoxy-2-methyl-1- 2.66^([a]) 352 oxopropan-2-yl 1275 Et O O 2-chloropyridin-3-yl 1-(prop-1-yn-1-yl)cyclopentyl 3.69^([a]) 358 1276 Et O O 2,3-dichloropyridin-4-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 2.96^([a]); 3.01^([c]) T2; 2.82^([c]) T1; 2.91^([b]) 398 1277 Et NH O 3-chloro-2-methylpyridin-4-yl 1-(pyridin-2-yl)ethyl 2.7^([a]) 370 1278 Et NH O 3-(difluoromethyl)-1- (2S)-3-methylbutan-2-yl 2.71^([a]) 340 methyl-1H-pyrazol-4-yl 1279 cPr NH O 3-(difluoromethyl)-1- 1-(1,3-thiazol-2-yl)ethyl 2.04^([a]) 393 methyl-1H-pyrazol-4-yl 1280 cPr NH O 3-(difluoromethyl)-1- 1-(pyridin-2-yl)ethyl 1.84^([a]) 387 methyl-1H-pyrazol-4-yl 1281 oxetan- O O 2-chloropyridin-3-yl (1S)-1-cyclopropylethyl 2.34^([c]) I2; 2.3^([c]) I1; 2.31^([b]) 3-yl 1282 Et NMe O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.91^([c]); 2.9^([b]) 1283 (2R)-3- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 4.02^([c]); 4.02^([b]) methylbu- tan-2-yl 1284 cBu O O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.79^([c]); 3.79^([b]) 1285 Et O O 3-chloro-2-methylpyridin-4-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 2.57^([a]) 377 1286 Me NMe O 3-(difluoromethyl)-1- (2S)-3-methylbutan-2-yl 2.45^([a]) 340 methyl-1H-pyrazol-4-yl 1287 2-MeOEt NH O 3-(difluoromethyl)-1- 1-(1,3-thiazol-2-yl)ethyl 1.96^([a]) 411 methyl-1H-pyrazol-4-yl 1288 2-MeOEt NH O 3-(difluoromethyl)-1- 1-(pyridin-2-yl)ethyl 1.75^([a]) 405 methyl-1H-pyrazol-4-yl 1289 Et NH O 2,3-dichloropyridin-4-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 2.57^([a]) 397 1290 Et O O 2-bromo-3-chloropyridin-4-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 3.02^([a]) 442 1291 allyl NH O 3-(difluoromethyl)-1- 1-(pyridin-2-yl)ethyl 2.02^([a]) 387 methyl-1H-pyrazol-4-yl 1292 allyl NH O 3-(difluoromethyl)-1- 1-(1,3-thiazol-2-yl)ethyl 2.2^([a]) 393 methyl-1H-pyrazol-4-yl 1293 Et NH O 3-(difluoromethyl)-1- 1-(pyridin-2-yl)ethyl 1.86^([a]) 375 methyl-1H-pyrazol-4-yl 1294 Et NH O 3-(difluoromethyl)-1- 1-(1,3-thiazol-2-yl)ethyl 2.05^([a]) 381 methyl-1H-pyrazol-4-yl 1295 Me NMe O 3-(difluoromethyl)-1- 1-(pyridin-2-yl)ethyl 1.59^([a]) 375 methyl-1H-pyrazol-4-yl 1296 Me NMe O 3-(difluoromethyl)-1- 1-(1,3-thiazol-2-yl)ethyl 1.81^([a]) 381 methyl-1H-pyrazol-4-yl 1297 propargyl NH O 3-(difluoromethyl)-1- 1-(1,3-thiazol-2-yl)ethyl 2.04^([a]) 391 methyl-1H-pyrazol-4-yl 1298 oxetan- NH O 3-(difluoromethyl)-1- (2S)-3-methylbutan-2-yl 1.84^([a]) 368 3-yl methyl-1H-pyrazol-4-yl 1299 2-cyano- NH O 3-(difluoromethyl)-1- (2S)-3-methylbutan-2-yl 2.44^([a]) 365 ethyl methyl-1H-pyrazol-4-yl 1300 Et O O 5-(difluoromethyl)-1- 1-(pyridin-2-yl)ethyl 2.41^([a]) 376 methyl-1H-pyrazol-4-yl 1301 Et O O 5-(difluoromethyl)-1- (2S)-3-methylbutan-2-yl 3.23^([a]) 341 methyl-1H-pyrazol-4-yl 1302 Et O O 5-(difluoromethyl)-1- (1S)-1-(1,3-thiazol-2-yl)ethyl 2.46^([a]) 382 methyl-1H-pyrazol-4-yl 1303 Et O O 5-(difluoromethyl)-1- (1S)-1-cyclopropylethyl 2.98^([a]) 339 methyl-1H-pyrazol-4-yl 1304 Et O O 5-(difluoromethyl)-1- cBu 2.84^([a]) 325 methyl-1H-pyrazol-4-yl 1305 Et NH O 2-bromo-3-chloropyridin-4-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 2.62^([a]) 441 1306 Et NH O 3-chloro-2-methylpyridin-4-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 2.18^([a]) 376 1307 Me O O 2-chloropyridin-3-yl (1S)-1-cyclopropylethyl 2.61^([c]) I2; 2.56^([c]) I1; 2.58^([b]) 1308 Et NH O 5-(difluoromethyl)-1- (1S)-1-(1,3-thiazol-2-yl)ethyl 2.11^([a]) 381 methyl-1H-pyrazol-4-yl 1309 Et NH O 5-(difluoromethyl)-1- (1S)-1-cyclopropylethyl 2.64^([a]) 338 methyl-1H-pyrazol-4-yl 1310 Et O O 2-chloropyridin-3-yl thieno[2,3-b]pyridin-5-yl 2.56^([c]); 2.49^([b]) 1311 Et O O 2-chloro-3-fluoropyridin-4-yl (2S)-3-methylbutan-2-yl 3.81^([a]) 340 1312 Et O O 2-chloro-3-fluoropyridin-4-yl 1-(pyridin-2-yl)ethyl 3^([a]) 375 1313 Et O O 2-chloro-3-fluoropyridin-4-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 2.96^([a]) 381 1314 Et O O 2-chloropyridin-3-yl (2S)-1-oxopropan-2-yl 1315 Et O O 2-bromo-3-fluoropyridin-4-yl (2S)-3-methylbutan-2-yl 3.87^([a]) 384 1316 Et NH O 2-chloro-3-fluoropyridin-4-yl (2S)-3-methylbutan-2-yl 3.44^([a]) 339 1317 Et O O 3-fluoro-2-methylpyridin-4-yl (2S)-3-methylbutan-2-yl 3.31^([a]) 320 1318 Et O O 2-chloro-3-fluoropyridin-4-yl (1R)-1-cyclopropylethyl 3.5^([a]) 338 1319 Et O O 3-fluoro-2-methylpyridin-4-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 2.48^([a]) 361 1320 Et O O 3-fluoro-2-methylpyridin-4-yl 1-(pyridin-2-yl)ethyl 2.5^([a]) 355 1321 Et O O 2-chloro-3-fluoropyridin-4-yl cBu 3.39^([a]) 324 1322 Et O O 2-chloropyridin-3-yl (1E,2S)-1-(methoxyimino)- 2.5^([c]) I2; 2.42^([c]) I1; 2.56^([c]); 2.49^([b]) propan-2-yl 1323 Et NH O 2-bromo-3-fluoropyridin-4-yl (2S)-3-methylbutan-2-yl 3.46^([a]) 383 1324 Et O O 2-chloro-3-fluoropyridin-4-yl 1-(methylamino)-1-oxopropan- 2.15^([a]) 355 2-yl 1325 Et O O 2-chloro-3-fluoropyridin-4-yl pent-3-yn-2-yl 3.39^([a]) 336 1326 R¹ & Y² = O 3-(difluoromethyl)-1- (2S)-3-methylbutan-2-yl 2.43^([a]) 382 morpholin-4-yl methyl-1H-pyrazol-4-yl 1327 R¹ & Y² = O 3-(difluoromethyl)-1- 1-(1,3-thiazol-2-yl)ethyl 1.79^([a]) 423 morpholin-4-yl methyl-1H-pyrazol-4-yl 1328 R¹ & Y² = O 3-(difluoromethyl)-1- 1-(pyridin-2-yl)ethyl 1.63^([a]) 417 morpholin-4-yl methyl-1H-pyrazol-4-yl 1329 Et NH O 2-chloro-3-fluoropyridin-4-yl 1-(pyridin-2-yl)ethyl 2.5^([a]) 374 1330 Et O O 2-bromo-3-fluoropyridin-4-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 3^([a]) 425 1331 Et O O 3-chloro-2-(methyl- (1S)-1-(1,3-thiazol-2-yl)ethyl 3.53^([a]) 409 sulfanyl)pyridin-4-yl 1332 Et O O 3-(difluoromethyl)-1- 1-methoxybutan-2-yl 2.71^([a]) 357 methyl-1H-pyrazol-4-yl 1333 Et O O 3-(difluoromethyl)-1- cyclohexyl 3.29^([a]) 353 methyl-1H-pyrazol-4-yl 1334 Et O O 3-(difluoromethyl)-1- 1-(dimethylamino)butan-2-yl 1.22^([a]) 370 methyl-1H-pyrazol-4-yl 1335 Et O O 3-(difluoromethyl)-1- 1-hydroxypentan-2-yl 2.28^([a]) 357 methyl-1H-pyrazol-4-yl 1336 Et O O 3-(difluoromethyl)-1- 1-(prop-1-yn-1-yl)cyclohexyl 3.71^([a]) 391 methyl-1H-pyrazol-4-yl 1337 Et O O 3-(difluoromethyl)-1- 4-ethoxycyclohexyl 3.08^([a]) 397 methyl-1H-pyrazol-4-yl 1338 Et O O 3-(difluoromethyl)-1- pentan-3-yl 3.15^([a]) 341 methyl-1H-pyrazol-4-yl 1339 Et O O 3-(difluoromethyl)-1- oxetan-3-yl 1.79^([a]) 327 methyl-1H-pyrazol-4-yl 1340 Et O O 3-(difluoromethyl)-1- (2-methyltetrahydrofuran-2- 2.54^([a]) 369 methyl-1H-pyrazol-4-yl yl)methyl 1341 Et O O 3-(difluoromethyl)-1- 1,3-dimethoxypropan-2-yl 2.42^([a]) 373 methyl-1H-pyrazol-4-yl 1342 Et O O 3-(difluoromethyl)-1- 1-cyanobutan-2-yl 2.39^([a]) 352 methyl-1H-pyrazol-4-yl 1343 Et O O 3-(difluoromethyl)-1- hexan-3-yl 3.51^([a]) 355 methyl-1H-pyrazol-4-yl 1433 Et O O 3-(difluoromethyl)-1- 1-methoxypentan-2-yl 3.06^([a]) 371 methyl-1H-pyrazol-4-yl 1435 Et O O 3-(difluoromethyl)-1- 1,3-diethoxypropan-2-yl 3.13^([a]) 401 methyl-1H-pyrazol-4-yl 1346 Et O O 3-(difluoromethyl)-1- 4,4,4-trifluorobutan-2-yl 2.77^([a]) 381 methyl-1H-pyrazol-4-yl 1347 Et O O 3-(difluoromethyl)-1- 2-(2-bromophenoxy)ethyl 3.35^([a]) 469 methyl-1H-pyrazol-4-yl 1348 Et O O 3-(difluoromethyl)-1- 2-(2-bromophenyl)propyl 3.69^([a]) 467 methyl-1H-pyrazol-4-yl 1349 Et O O 3-(difluoromethyl)-1- 2-ethoxy-2-oxo-1-phenylethyl 3.25^([a]) 433 methyl-1H-pyrazol-4-yl 1350 Et O O 3-(difluoromethyl)-1- 1-ethoxy-3-methylbutan-2-yl 3.39^([a]) 385 methyl-1H-pyrazol-4-yl 1351 Et O O 3-(difluoromethyl)-1- 1-ethoxybutan-2-yl 3.08^([a]) 371 methyl-1H-pyrazol-4-yl 1352 Et O O 3-(difluoromethyl)-1- 2-methoxycyclopentyl 2.78^([a]) 369 methyl-1H-pyrazol-4-yl 1353 Et O O 3-(difluoromethyl)-1- 2-ethoxycyclopentyl 3.21^([a]) 383 methyl-1H-pyrazol-4-yl 1354 Et O O 3-(difluoromethyl)-1- 1-ethoxypentan-2-yl 3.44^([a]) 385 methyl-1H-pyrazol-4-yl 1355 Et O O 3-(difluoromethyl)-1- thietan-3-yl 2.54^([a]) 343 methyl-1H-pyrazol-4-yl 1356 Et O O 2-chloropyridin-3-yl oxetan-3-yl 1.84^([a]) 308 1357 Et O O 2-chloropyridin-3-yl (2-methyltetrahydrofuran-2- 2.7^([a]) 350 yl)methyl 1358 Et O O 2-chloropyridin-3-yl 1,3-dimethoxypropan-2-yl 2.56^([a]) 354 1359 Et O O 2-chloropyridin-3-yl 1-cyanobutan-2-yl 2.51^([a]) 333 1360 Et O O 3-(difluoromethyl)-1- 1-(4-chlorophenyl)cyclopropyl 3.58^([a]) 421 methyl-1H-pyrazol-4-yl 1361 Et O O 3-(difluoromethyl)-1- 1-(3-chlorophenyl)cyclopropyl 3.51^([a]) 421 methyl-1H-pyrazol-4-yl 1362 Et O O 3-(difluoromethyl)-1- 1-(2-chlorophenyl)cyclopropyl 3.35^([a]) 421 methyl-1H-pyrazol-4-yl 1363 Et O O 3-(difluoromethyl)-1- (4-chlorophenyl)- 3.89^([a]) 435 methyl-1H-pyrazol-4-yl (cyclopropyl)methyl 1364 Et O O 3-(difluoromethyl)-1- 1-phenylcyclopropyl 3.21^([a]) 387 methyl-1H-pyrazol-4-yl 1365 Et O O 3-(difluoromethyl)-1- 1-(2-methylphenyl)ethyl 3.46^([a]) 389 methyl-1H-pyrazol-4-yl 1366 Et O O 2-chloropyridin-3-yl 4,4,4-trifluorobutan-2-yl 2.92^([a]) 362 1367 Et O O 2-chloropyridin-3-yl 1-methoxybutan-2-yl 2.92^([a]) 338 1368 Et O O 2-chloropyridin-3-yl 1-hydroxypentan-2-yl 2.45^([a]) 338 1369 Et O O 2-chloropyridin-3-yl 1,1-dioxidotetrahydrothiophen- 1.84^([a]) 370 3-yl 1370 Et O O 2-chloropyridin-3-yl 4-ethoxycyclohexyl 3.31^([a]) 378 1371 Et O O 2-chloropyridin-3-yl pentan-3-yl 3.35^([a]) 322 1372 Et O O 2-chloropyridin-3-yl 1-ethoxybutan-2-yl 3.31^([a]) 352 1373 Et O O 2-chloropyridin-3-yl 2-ethoxycyclopentyl 3.44^([a]) 364 1374 Et O O 2-chloropyridin-3-yl thietan-3-yl 2.64^([a]) 324 1375 Et O O 2-chloropyridin-3-yl 1-methoxypentan-2-yl 3.31^([a]) 352 1376 Et O O 2-chloropyridin-3-yl 1,3-diethoxypropan-2-yl 3.33^([a]) 382 1377 Et O O 2-chloropyridin-3-yl 2-(2-bromophenoxy)ethyl 3.53^([a]) 450 1378 Et O O 2-chloropyridin-3-yl 2-(2-bromophenyl)propyl 3.94^([a]) 448 1379 Et O O 2-chloropyridin-3-yl 2-ethoxy-2-oxo-1-phenylethyl 3.39^([a]) 414 1380 Et O O 2-chloro-6-methylpyridin-3-yl 1-(pyridin-2-yl)ethyl 2.64^([c]) T2; 2.53^([c]) T1; 2.67^([b]) 1381 Et O O 2,6-dichloropyridin-3-yl 1-(pyridin-2-yl)ethyl 2.93^([c]) T1; 3.09^([c]) T2; 3.06^([b]) 1382 Et O O 3-chloro-2-propylpyridin-4-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 3.27^([a]) 405 1383 Et O O 3-chloro-2-ethylpyridin-4-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 2.92^([a]) 391 1384 Et O O 3-chloro-2-(2- (1S)-1-(1,3-thiazol-2-yl)ethyl 3.64^([a]) 419 methylpropyl)pyridin-4-yl 1385 Et O O 3-chloro-2-phenylpyridin-4-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 3.31^([a]) 439 1386 Et O O 2,3-dichloropyridin-4-yl pent-3-yn-2-yl 3.44^([a]) 353 1387 Et O O 2,3-dichloropyridin-4-yl (2S)-1-(methylamino)-1- 2.1^([a]) 372 oxopropan-2-yl 1388 Et O O 2,3-dichloropyridin-4-yl 2-(methylsulfanyl)phenyl 3.89^([a]) 409 1389 Et O O 2,3-dichloropyridin-4-yl 1-(5-methyl-1,3-thiazol-2- 3.33^([a]) 412 yl)ethyl 1390 Et O O 2,3-dichloropyridin-4-yl pentan-2-yl 3.99^([a]) 357 1391 Et O O 2-bromo-3-chloropyridin-4-yl 1-(pyridin-2-yl)ethyl 3.09^([a]) 436 1392 Et O O 2,3-dichloropyridin-4-yl (2S)-1-methoxypropan-2-yl 3.06^([a]) 359 1393 Et O O 3-chloro-2-(methyl- 1-(pyridin-2-yl)ethyl 3.35^([a]) 403 sulfanyl)pyridin-4-yl 1394 Et O O 3-(trifluoromethyl)pyridin- 1-(pyridin-2-yl)ethyl 2.7^([a]) 391 4-yl 1395 Et O O 2-bromo-3-fluoropyridin-4-yl 1-(pyridin-2-yl)ethyl 3^([a]) 419 1396 Et O O 3-chloro-2-ethylpyridin-4-yl 1-(pyridin-2-yl)ethyl 2.96^([a]) 385 1397 Et O O 3-chloro-2-propylpyridin-4-yl 1-(pyridin-2-yl)ethyl 3.29^([a]) 399 1398 Et O O 3-chloro-2-phenylpyridin-4-yl 1-(pyridin-2-yl)ethyl 3.33^([a]) 433 1399 Et O O 3-chloro-2-ethylpyridin-4-yl (2S)-3-methylbutan-2-yl 4.02^([a]) 350 1400 Et O O 3-chloro-2-propylpyridin-4-yl (2S)-3-methylbutan-2-yl 4.41^([a]) 364 1401 Et O O 3-chloro-2-(methyl- (2S)-3-methylbutan-2-yl 4.44^([a]) 368 sulfanyl)pyridin-4-yl 1402 Et O O 3-chloro-2-(2-methyl- (2S)-3-methylbutan-2-yl 4.81^([a]) 378 propyl)pyridin-4-yl 1403 Et O O 3-chloro-2-phenylpyridin-4-yl (2S)-3-methylbutan-2-yl 4.34^([a]) 398 1404 Et O O 3-bromo-2-chloropyridin-4-yl 1-(pyridin-2-yl)ethyl 3.06^([a]) 436 1405 Et O O 3-bromo-2-chloropyridin-4-yl (2S)-3-methylbutan-2-yl 3.92^([a]) 401 1406 Et O O 3-bromo-2-chloropyridin-4-yl 1-(1,3-thiazol-2-yl)ethyl 2.96^([a]) 442 1407 propargyl NH O 3-(difluoromethyl)-1- 1-(pyridin-2-yl)ethyl 1.89^([a]) 385 methyl-1H-pyrazol-4-yl 1408 Et NH O 3-bromo-2-chloropyridin-4-yl (2S)-3-methylbutan-2-yl 3.53^([a]) 400 1409 Et O O 2,3-dibromopyridin-4-yl 1-(pyridin-2-yl)ethyl 3.11^([a]) 481 1410 Et O O 2,3-dibromopyridin-4-yl (2S)-3-methylbutan-2-yl 3.96^([a]) 446 1411 Et NH O 3-bromo-2-chloropyridin-4-yl 1-(pyridin-2-yl)ethyl 2.55^([a]) 435 1412 Et O O 2-chloropyridin-3-yl (3-chloropyridin-2-yl)methyl 2.78^([a]) 378 1413 Et O O 2-chloropyridin-3-yl (3-chloropyridin-2-yl)methyl 2.77^([a]) 377 1414 Et O O 2-chloropyridin-3-yl 1-(furan-1-yl)ethyl 2.92^([a]) 346 1415 Et O O 2-chloropyridin-3-yl 1-(pyrazin-2-yl)ethyl 2.13^([a]) 358 1416 Et O O 2-chloropyridin-3-yl (1S)-1-(4-cyclopropyl-1,3- 3.37^([a]) 403 thiazol-2-yl)ethyl 1417 Et O O 3-(difluoromethyl)-1- 1,1,1-trifluoro-4-methylpentan- 3.8^([a]) 409 methyl-1H-pyrazol-4-yl 2-yl 1418 Et O O 3-(difluoromethyl)-1- tBu 2.66^([a]) 327 methyl-1H-pyrazol-4-yl 1419 Et O O 3-(difluoromethyl)-1- iPr 2.53^([a]) 313 methyl-1H-pyrazol-4-yl 1420 Et O O 3-(difluoromethyl)-1- 1,1-dioxidotetrahydrothiophen- 1.79^([a]) 389 methyl-1H-pyrazol-4-yl 3-yl 1421 Et O O 3-(difluoromethyl)-1- 2-methylbutan-2-yl 2.96^([a]) 341 methyl-1H-pyrazol-4-yl 1422 Et O O 3-(difluoromethyl)-1- 1-cyano-2-methylpropyl 2.76^([a]) 352 methyl-1H-pyrazol-4-yl 1423 Et O O 3-(difluoromethyl)-1- (3-methyloxetan-3-yl)methyl 2.04^([a]) 355 methyl-1H-pyrazol-4-yl 1424 Et O O 3-(difluoromethyl)-1- 1,1,1-trifluoropentan-2-yl 3.53^([a]) 395 methyl-1H-pyrazol-4-yl 1425 Et O O 2-chloropyridin-3-yl 2-methylbutan-2-yl 3.23^([a]) 322 1426 Et O O 3-(difluoromethyl)-1- 2-(methylsulfanyl)-5- 3.67^([a]) 461 methyl-1H-pyrazol-4-yl (trifluoromethyl)phenyl 1427 Et O O 3-(difluoromethyl)-1- 2-(1,1,1,3,3,3-hexafluoro-2- 3.25^([a]) 513 methyl-1H-pyrazol-4-yl hydroxypropan-2-yl)phenyl 1428 Et O O 3-(difluoromethyl)-1- 3,3,3-trifluoro-1-phenylpropyl 3.37^([a]) 443 methyl-1H-pyrazol-4-yl 1429 Et O O 2-chloropyridin-3-yl (3-methyloxetan-3-yl)methyl 2.11^([a]) 336 1430 Et O O 2-chloropyridin-3-yl 1-(prop-1-yn-1-yl)cyclohexyl 4.06^([a]) 372 1431 Et O O 2-chloropyridin-3-yl 1-ethoxy-3-methylbutan-2-yl 3.69^([a]) 366 1432 Et O O 2-chloropyridin-3-yl 2-methoxycyclopentyl 2.96^([a]) 350 1433 Et O O 2-chloropyridin-3-yl 1-ethoxypentan-2-yl 3.73^([a]) 366 1434 Et O O 2-chloropyridin-3-yl hexan-3-yl 3.8^([a]) 336 1435 Et O O 2-chloropyridin-3-yl 1-cyano-2-methylpropyl 2.76^([a]) 333 1436 Et O O 2-chloropyridin-3-yl 6,7-dihydro-5H- 2.4^([a]) 369 cyclopenta^([b])pyridin-7-yl 1437 Et O O 2-chloropyridin-3-yl 1-(6-chloropyridin-3-yl)ethyl 2.8^([a]) 392 1438 Et O O 2-chloropyridin-3-yl 1-(6-methoxypyridin-2-yl)ethyl 3.5^([a]) 387 1439 Et O O 2-chloropyridin-3-yl 1-(6-chloropyridin-2-yl)ethyl 3.2^([a]) 392 1440 Et O O 2-chloropyridin-3-yl 1-(6-methylpyridin-2-yl)ethyl 2.56^([a]) 371 1441 Et O O 2-chloropyridin-3-yl 1-(quinolin-2-yl)ethyl 3.37^([a]) 407 1442 Et O O 2-chloropyridin-3-yl 1-(4-methylpyridin-2-yl)ethyl 2.6^([a]) 371 1443 Et O O 2-chloropyridin-3-yl (1E,2S)-1-(hydroxyimino)- 1.68^([c]) T1; 1.86^([c]) T2; 1.78^([b]) propan-2-yl 1444 Et O O 2-chloropyridin-3-yl 1-(2-chloro-1,3-thiazol-5- 3.1^([a]) 397 yl)ethyl 1445 Et O O 2-chloropyridin-3-yl 1-(5-chloropyridin-2-yl)ethyl 3.3^([a]) 391 1446 Et O O 2-chloropyridin-3-yl 1-(4-chloro-6-methylpyridin-2- 3.4^([a]) 405 yl)ethyl 1447 Et O O 2-chloropyridin-3-yl 1-(2-phenyl-1,3-thiazol-4- 4^([a]) 439 yl)ethyl 1448 Et O O 2-chloropyridin-3-yl 1-[3-(methylsulfanyl)pyridin-2- 3.1^([a]) 403 yl]ethyl 1449 Et O O 2-chloropyridin-3-yl 1-(4-chloropyridin-2-yl)ethyl 3^([a]) 391 1450 allyl O O 2,6-dichloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 3.24^([c]) T2; 3.04^([c]) T1; 3.16^([b]) 1451 cPr NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.74^([c]); 2.76^([b]) 1452 thietan-3- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.22^([c]); 3.22^([b]) yl 1453 cBu NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.44^([c]); 3.44^([b]) 1454 ethoxy NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.44^([c]); 2.44^([b]) 1455 oxetan-3- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.24^([c]); 2.26^([b]) yl 1456 2-fluoro- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.83^([c]); 2.83^([b]) cyclo- propyl 1457 Et O O 2-[4-(trifluoromethyl)- (2S)-3-methylbutan-2-yl 4.23^([c]); 4.25^([b]) phenyl]pyridin-3-yl 1458 allyl NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3^([c]); 3^([b]) 1459 OMe NH O 2,6-dichloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2^([c]) T1; 2.12^([c]) T2; 1.94^([b]) 1460 Me NH O 2,6-dichloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.37^([c]) T2; 2.19^([c]) T1; 2.29^([b]) 1461 prop-2- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.66^([c]); 2.62^([b]) en-1- yloxy 1462 Et O O 4-chloro-1,3-thiazol-5-yl 1-(pyridin-2-yl)ethyl 2.59^([a]) 363 1463 Et O O 4-chloro-1,3-thiazol-5-yl 1-(1,3-thiazol-2-yl)ethyl 2.59^([a]) 369 1464 Et O O 4-chloro-1,3-thiazol-5-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 2.59^([a]) 369 1465 Et O O 4-chloro-1,3-thiazol-5-yl cBu 3^([a]) 312 1466 Et O O 4-chloro-1,3-thiazol-5-yl (1S)-1-cyclopropylethyl 2.02^([a]) 326 1467 Et O O 4-chloro-1,3-thiazol-5-yl (2S)-1-methoxypropan-2-yl 2.61^([a]) 330 1468 Et O O 4-chloro-1,3-thiazol-5-yl (2S)-3-methylbutan-2-yl 3.46^([a]) 328 1469 1,1- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.28^([c]); 2.29^([b]) dioxido- thietan-3- yl 1470 (2R)-1- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.95^([c]) I2; 2.85^([c]) I1; 2.96^([b]) I2; methoxy- 2.87^([b]) I1 1-oxopro- pan-2-yl 1471 Et NH O 2,6-dichloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.54^([c]) T1; 2.73^([c]) T2; 2.65^([b]) 1472 Et O O 2-(4-methoxyphenyl)- (2S)-3-methylbutan-2-yl 3.54^([c]); 3.59^([b]) pyridin-3-yl 1473 Et O O 2-(prop-2-en-1- 1-(pyridin-2-yl)ethyl 1.78^([c]); 2.05^([b]) yloxy)pyridin-2-yl 1474 Et S O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.87^([a]) 338 1475 Et O O 2-(3,4-dichlorophenyl)- (2S)-3-methylbutan-2-yl 4.56^([c]); 4.56^([b]) pyridin-3-yl 1476 Et O O 4-chloro-1,3-thiazol-5-yl (2S)-1-(methylamino)-1- 1.81^([a]) 343 oxopropan-2-yl 1477 Et O O 4-chloro-1,3-thiazol-5-yl (1R)-1-(2,6- 4^([a]) 430 dichlorophenyl)ethyl 1478 Et O O 4-chloro-1,3-thiazol-5-yl (5,6-dimethylpyridin-2- 1.94^([a]) 377 yl)methyl 1479 H O O 2-chloropyridin-3-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 1.01^([a]) 335 1480 Et O O 4-chloro-1,3-thiazol-5-yl 3-methoxybutan-2-yl 2.94^([a]) 344 1481 Et O O 4-chloro-1,3-thiazol-5-yl 3-methylpentan-2-yl 3.92^([a]) 342 1482 Et O O 5-chloro-1-methyl-1H- (1S)-1-cyclopropylethyl 2.98^([a]) 323 pyrazol-4-yl 1483 Et O O 5-chloro-1-methyl-1H- 1-(1,3-thiazol-2-yl)ethyl 2.42^([a]) 366 pyrazol-4-yl 1484 Et O O 5-chloro-1-methyl-1H- 1-(pyridin-2-yl)ethyl 2.35^([a]) 360 pyrazol-4-yl 1485 Et O O 5-chloro-1-methyl-1H- (2S)-3-methylbutan-2-yl 3.25^([a]) 325 pyrazol-4-yl 1486 Et O O 5-chloro-1-methyl-1H- (2S)-1-methoxypropan-2-yl 2.42^([a]) 327 pyrazol-4-yl 1487 Et O O 5-chloro-1-methyl-1H- cBu 2.82^([a]) 309 pyrazol-4-yl 1488 Et O O 5-chloro-1-methyl-1H- (2S)-1-(methylamino)-1- 1.63^([a]) 340 pyrazol-4-yl oxopropan-2-yl 1489 Et S O 2-chloropyridin-3-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 2.9^([a]) 379 1490 allyl O O 2-chloropyridin-3-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 2.62^([a]) 1491 R¹ & Y² = O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.02^([a]) 347 pyrrolidin-1-yl 1492 2-MeOEt NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.73^([a]) 351 1493 cyclo- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.9^([a]) 361 pentyl 1494 iBu NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.74^([a]) 349 1495 2,2- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.72^([a]) 361 dimethyl- cyclopropyl 1496 Et O O quinolin-4-yl (2S)-3-methylbutan-2-yl 3.29^([a]) 338 1497 Et O O quinolin-4-yl 1-(pyridin-2-yl)ethyl 2.5^([a]) 373 1498 Et O O quinolin-4-yl cBu 2.88^([a]) 322 1499 Et O O quinolin-4-yl (2S)-1-methoxypropan-2-yl 2.5^([a]) 340 1500 Et O O quinolin-4-yl 1-cyclopropylethyl 3.02^([a]) 336 1501 Et O O 5-chloro-1-methyl-1H- (1S)-1-(1,3-thiazol-2-yl)ethyl 2.42^([a]) 366 pyrazol-4-yl 1502 Et O O quinolin-4-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 2.5^([a]) 379 1503 Et O O quinolin-4-yl (2S)-1-(methylamino)-1- 1.8^([a]) 353 oxopropan-2-yl 1504 Et O O pyridin-3-yl (2S)-3-methylbutan-2-yl 2.61^([c]); 2.67^([b]) 1505 Et O O 2-(thiophen-2-yl)pyridin-3-yl (2S)-3-methylbutan-2-yl 3.7^([c]); 3.7^([b]) 1506 Et O O 2-(prop-2-en-1- 1-(1,3-thiazol-2-yl)ethyl 2.03^([c]); 2.03^([b]) yloxy)pyridin-3-yl 1507 R¹ & Y² = O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.27^([a]) 379 thiomorpholin-4-yl 1508 R¹ & Y² = O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.48^([a]) 361 piperidin-1-yl 1509 R¹ & Y² = O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.19^([a]) 365 1,3-thiazolidin-3-yl 1510 2-(methyl- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.29^([a]) 367 sulfanyl)- ethyl 1511 2-methyl- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 4.01^([a]) 361 cyclobutyl 1512 3-methyl- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 4.01^([a]) 361 cyclobutyl 1513 cPr NMe O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.02^([a]) 347 1514 Et NOMe O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.15^([a]) 351 1515 pyridin-4- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 1.58^([a]) 370 yl 1516 pyridin-2- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.21^([a]) 370 yl 1517 pyridin-2- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 1.94^([a]) 384 ylmethyl 1518 R¹ & Y² = O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.58^([a]) 363 morpholin-4-yl 1519 Et O O 2-(thiophen-3-yl)pyridin-3-yl (2S)-3-methylbutan-2-yl 3.55^([c]); 3.55^([c]); 3.57^([b]); 3.57^([b]) 1520 Et O O 2-chloropyridin-3-yl 1-(5-methyl-1,3-thiazol-2- 2.92^([a]) yl)ethyl 1521 Et O O 2-chloropyridin-3-yl 4-methylpent-1-yn-3-yl 3.37^([a]) 1522 Et O O 2-chloropyridin-3-yl 1-(trimethylsilyl)ethyl 3.87^([a]) 1523 Et O O 2-chloropyridin-3-yl (1S)-1-(2,6-dichlorophenyl)ethyl 3.73^([a]) 1524 Et O O 2-chloropyridin-3-yl 1-(2-methyl-1,3-thiazol-4- 2.84^([a]) yl)ethyl 1525 Et O O 2-chloropyridin-3-yl 3-methylpentan-2-yl 3.76^([a]) 336 1526 Et O O 2-chloropyridin-3-yl (5,6-dimethylpyridin-2- 1.91^([a]) 371 yl)methyl 1527 Et O O 2-chloropyridin-3-yl 3-methoxybutan-2-yl 2.8^([a]) 1528 Et O O 2-chloropyridin-3-yl 1-[4-(trifluoromethyl)pyrimidin- 2.63^([a]) 5-yl]ethyl 1529 Et O O 2-chloropyridin-3-yl 1-(imidazo[2,1-b][1,3]thiazol-6- 2.35^([a]) yl)ethyl 1530 Et O O 2-chloropyridin-3-yl 1-(2-bromophenyl)ethyl 3.89^([a]) 1531 Et O O 2-chloropyridin-3-yl 1-(tetrahydrofuran-2-yl)ethyl 2.71^([a]) 1532 Et O O 2-chloropyridin-3-yl 1-(2-fluorophenyl)ethyl 3.48^([a]) 1533 Et O O 2-chloropyridin-3-yl 1-(1-methylcyclopropyl)ethyl 3.46^([a]) 1534 Et O O 2-chloropyridin-3-yl (1S)-1-(2,6- 3.96^([a]) dimethylphenyl)ethyl 1535 Et O O 2-chloropyridin-3-yl (1S)-1-(2,6-difluorophenyl)ethyl 3.27^([a]) 1536 Et O O 2-chloropyridin-3-yl 1-(4-methyl-1,3-thiazol-2- 2.88^([a]) yl)ethyl 1537 Et O O 2-chloropyridin-3-yl 2-methyl-2H-indazol-7-yl 2.68^([a]) 1538 Et O O 2-chloropyridin-3-yl 2-methyl-1-(4-methylpyrimidin- 2.28^([a]) 5-yl)propyl 1539 Et O O 2-chloropyridin-3-yl (2S)-1-(benzyloxy)-1- 3.53^([a]) oxopropan-2-yl 1540 Et O O 2-(furan-2-yl)pyridin-3-yl (2S)-3-methylbutan-2-yl 3.21^([c]) I2; 3.21^([c]) I2; 3.19^([c]) I1; 3.19^([c]) I1; 3.21^([b]) I2; 3.19^([b]) I1; 3.19^([b]) I1; 3.21^([b]) I2 1541 Et O O 2-(4-fluorophenyl)pyridin- (2S)-3-methylbutan-2-yl 3.7^([c]); 3.7^([c]); 3.68^([b]); 3.7^([b]) 3-yl 1542 Et O O 5-chloro-1-methyl-1H- (5,6-dimethylpyridin-2- 1.66^([a]) 374 pyrazol-4-yl yl)methyl 1543 Et O O 5-chloro-1-methyl-1H- 3-methoxybutan-2-yl 2.67^([a]) 341 pyrazol-4-yl 1544 Et O O 5-chloro-1-methyl-1H- 3-methylpentan-2-yl 3.6^([a]) 339 pyrazol-4-yl 1545 Et O O 2-bromopyridin-3-yl (2S)-3-methylbutan-2-yl 3.27^([c]); 3.27^([c]); 3.26^([b]); 3.27^([b]) 1546 Et O O 2-bromopyridin-3-yl 1-(pyridin-2-yl)ethyl 2.46^([c]) T2; 2.47^([c]) T2; 2.34^([c]) T1; 2.35^([c]) T1; 2.49^([b]); 2.5^([b]) 1547 Et O O 2-bromopyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.35^([c]) T1; 2.34^([c]) T1; 2.53^([c]) T2; 2.52^([c]) T2; 2.44^([b]); 2.44^([b]) 1548 Et O O 2-chloropyridin-3-yl 1-(4,5,6,7-tetrahydro-1,3- 3.21^([a]) 417 benzothiazol-2-yl)ethyl 1549 Et O O 2-chloropyridin-3-yl 2,2,2-trifluoro-1-(pyridin-2- 3.17^([a]) 411 yl)ethyl 1550 Et O O 2-chloropyridin-3-yl 1-phenylcyclobutyl 3.73^([a]) 382 1551 Et O O 2-chloropyridin-3-yl 1-(ethoxycarbonyl)cyclobutyl 3.17^([a]) 378 1552 Et O O 2-chloropyridin-3-yl 1-(2,5-dimethyl-1,3-thiazol-4- 2.84^([a]) 391 yl)ethyl 1553 Et O O 2-chloropyridin-3-yl 1,3-benzothiazol-4-yl 2.61^([a]) 385 1554 Et O O 2-chloropyridin-3-yl [3-(trifluoromethyl)pyridin-2- 3^([a]) 411 yl]methyl 1555 Et O O 2-chloropyridin-3-yl 2-methyl-1,3-benzoxazol-4-yl 3^([a]) 383 1556 Et O O 2-chloropyridin-3-yl 2,1,3-benzothiadiazol-4-yl 3.17^([a]) 386 1557 Et O O 2-chloropyridin-3-yl 2-methyl-1-[4- 3.55^([a]) 454 (trifluoromethyl)pyrimidin-5- yl]propyl 1558 Et O O 2-chloropyridin-3-yl 1-(2,5-dichlorophenyl)ethyl 4.13^([a]) 424 1559 Et O O 5-chloro-1-methyl-1H- (1R)-1-(2,6- 3.78^([a]) 429 pyrazol-4-yl dichlorophenyl)ethyl 1560 Et O O 3-(dichloromethyl)-1- 1-cyclopropylethyl 3.23^([a]) 371 methyl-1H-pyrazol-4-yl 1561 Et O O 3-(dichloromethyl)-1- 1-cyclobutylethyl 3.67^([a]) 385 methyl-1H-pyrazol-4-yl 1562 Et O O 3-(dichloromethyl)-1- (2R)-3-methylbutan-2-yl 3.46^([a]) 373 methyl-1H-pyrazol-4-yl 1563 2-fluoro- NH O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2^([a]) 380 ethyl 1564 Et O O 3-(dichloromethyl)-1- (1R)-1-(1,3-thiazol-2-yl)ethyl 2.75^([a]) 414 methyl-1H-pyrazol-4-yl 1565 Et O O 3-(dichloromethyl)-1- 1-(pyridin-2-yl)ethyl 2.7^([a]) 408 methyl-1H-pyrazol-4-yl 1566 Et O O 3-(dichloromethyl)-1- cBu 3.09^([a]) 357 methyl-1H-pyrazol-4-yl 1567 Et O O 3-(dichloromethyl)-1- (2R)-1-methoxypropan-2-yl 2.76^([a]) 375 methyl-1H-pyrazol-4-yl 1568 Et O O 2-(3-chlorophenyl)pyridin- (2S)-3-methylbutan-2-yl 4.07^([c]); 4.09^([b]) 3-yl 1569 Et O O 2-(4- (2S)-3-methylbutan-2-yl hydrophenyl)pyridin-3-yl 1570 Et O O 2-(benzyloxy)pyridin-3-yl (1S)-1-cyclopropylethyl 3.08^([c]); 3.08^([b]) 1571 H O O 2-chloropyridin-3-yl 1-(pyridin-2-yl)ethyl 1.37^([a]) 329 1572 allyl O O 2-chloropyridin-3-yl 1-(pyridin-2-yl)ethyl 2.66^([a]) 369 1573 Et O O 3-(dichloromethyl)-1- (2S)-1-(methylamino)-1- 3.9^([a]) 388 methyl-1H-pyrazol-4-yl oxopropan-2-yl 1574 Et O O 3-(dichloromethyl)-1- 1-(2,6-dichlorophenyl)ethyl 3.94^([a]) 477 methyl-1H-pyrazol-4-yl 1575 Et O O 3-(dichloromethyl)-1- (5,6-dimethylpyridin-2- 2.07^([a]) 422 methyl-1H-pyrazol-4-yl yl)methyl 1576 Et O O 3-(dichloromethyl)-1- 3-methoxybutan-2-yl 2.98^([a]) 389 methyl-1H-pyrazol-4-yl 1577 Et O O 3-(dichloromethyl)-1- 3-methylpentan-2-yl 3.8^([a]) 387 methyl-1H-pyrazol-4-yl 1578 Et O O 2,5-dichlorothiophen-3-yl (1S)-1-(1,3-thiazol-2-yl)ethyl 3.58^([a]) 402 1579 Et O O 2,5-dichlorothiophen-3-yl 1-(pyridin-2-yl)ethyl 3.59^([a]) 369 1580 Et O O 2,5-dichlorothiophen-3-yl (2S)-3-methylbutan-2-yl 4.68^([a]) 361 1581 Et O O 2,5-dichlorothiophen-3-yl cBu 4.26^([a]) 345 1582 Et O O 2-chloropyridin-3-yl 6-methylheptan-2-yl 4.47^([c]) I2; 4.45^([c]) I1; 4.47^([b]) 1583 OMe NH O 2-chloropyridin-3-yl 1-(pyridin-2-yl)ethyl 1.46^([a]) 358 1584 Et NH O 2-chloropyridin-3-yl 1-(pyridin-2-yl)ethyl 1.93^([a]) 356 1585 Et O O 2-(4-cyanophenyl)pyridin- (2S)-3-methylbutan-2-yl 3.26^([c]) I1; 3.29^([c]) I2; 3.29^([b]) I1; 3-yl 3.3^([b]) I2 1586 Et O O 2-[4-(trifluorometh- (2S)-3-methylbutan-2-yl 4.39^([c]); 4.41^([b]) oxy)phenyl]pyridin-3-yl 1587 Et O O 2,5-dichlorothiophen-3-yl 1-cyclopropylethyl 4.43^([a]) 359 1588 Et O O 2,5-dichlorothiophen-3-yl (2S)-1-methoxypropan-2-yl 3.78^([a]) 363 1589 Et O O 2,5-dichlorothiophen-3-yl 1-cyclobutylethyl 5.03^([a]) 373 1590 Et O O 2-chloropyridin-3-yl 2-fluorophenyl 2.87^([c]); 2.85^([b]) 1591 Et O O 2-(pyrimidin-5-yl)pyridin- (2S)-3-methylbutan-2-yl 2.42^([c]) I2; 2.38^([c]) I1; 2.42^([b]) 3-yl 1592 Et O O 2-chloropyridin-3-yl 1-methyl-2-(methylsulfanyl)- 3.01^([c]); 3.01^([b]) 1H-pyrrol-3-yl 1593 2-fluoro- NH O 2-chloropyridin-3-yl 3-methylbutan-2-yl 2.76^([a]) 339 ethyl 1594 R¹ & Y² = O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 2.76^([a]) 420 2-methyl-1,3- thiazolidin-3-yl 1595 R¹ & Y² = O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 1.84^([a]) 404 morpholin-4-yl 1596 2-methoxy- NH O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 1.9^([a]) 406 2-oxoethyl 1597 Et O O 2-chloropyridin-3-yl 3,4-difluorophenyl 3^([c]); 2.96^([b]) 1598 ethoxy NH O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 1.8^([a]) 378 1599 R¹ & Y² = O 2-chloropyridin-3-yl 1-(1,3-thiazol-2-yl)ethyl 1.9^([a]) 390 1,2-oxazolidin-2-yl 1600 Et O O 2-chloropyridin-3-yl 2,4-difluorophenyl 2.95^([c]); 2.9^([b]) 1601 Et O O 2-chloropyridin-3-yl 1-methyl-2-(methylsulfonyl)- 2.07^([c]); 2.08^([b]) 1H-pyrrol-3-yl 1602 allyl O O 2-chloropyridin-3-yl 2-(methylsulfanyl)phenyl 3.32^([c]); 3.32^([b]) 1603 Et O O 2,5-dichlorothiophen-3-yl 3-methoxybutan-2-yl 4.02^([a]) 377 1604 Et O O 2-chloropyridin-3-yl 2,3-difluorophenyl 3^([c]); 2.88^([b]) 1605 Et O O 2-chloropyridin-3-yl 5,6,7,8-tetrahydroquinolin-8-yl 3^([a]) 383 1606 Et O O 2-chloropyridin-3-yl 1-cyclopentylethyl 3.9^([a]) 348 1607 Et O O 2-chloropyridin-3-yl 1-methylcyclobutyl 3.11^([a]) 320 1608 Et O O 2-chloropyridin-3-yl 1-(1H-pyrazol-5-yl)ethyl 2.1^([a]) 346 1609 Et O O 2-chloropyridin-3-yl 2,5-difluorophenyl 2.95^([c]); 2.83^([b]) 1610 Et O O 2-chloropyridin-3-yl 3-fluoro-2-methylphenyl 3.26^([c]); 3.24^([b]) 1611 Et O O 2-chloropyridin-3-yl 3-fluoro-2-methoxyphenyl 3.13^([c]); 3.13^([b]) 1612 R¹ & Y² = O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.55^([a]) 349 1,2-oxazolidin-2-yl 1613 1-methoxy- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.75^([a]) 363 cyclopropyl 1614 dimethyl- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 2.08^([a]) 336 amino 1615 R¹ & Y² = O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.6^([a]) 379 2-methyl-1,3- thiazolidin-3-yl 1616 Et NH O 2-chloropyridin-3-yl 2-(methylsulfanyl)phenyl 2.85^([c]); 2.82^([b]) 1617 Et O O 6-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.39^([c]); 3.41^([b]) 1618 R¹ & Y² = O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 3.1^([a]) 365 1,3-thiazolidin-3-yl 1619 (1Z)-N- NH O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 1.88^([a]) 364 methoxy- ethani- midoyl 1620 OMe NH O 2-chloropyridin-3-yl 2-(methylsulfanyl)phenyl 2.19^([c]); 1.96^([b]) 1621 Et O O 3-chloro-2-(trifluoro- cBu 3.78^([a]) 374 methyl)pyridin-4-yl 1622 Et O O 3-chloro-2-(trifluoro- (1S)-1-cyclopropylethyl 3.85^([a]) 388 methyl)pyridin-4-yl 1623 Et O O 3-chloro-2-(trifluoro- (2S)-1-methoxypropan-2-yl 3.46^([a]) 392 methyl)pyridin-4-yl 1624 Et O O 3-chloro-2-(trifluoro- 1-(tetrahydrofuran-2-yl)ethyl 3.62^([a]) 418 methyl)pyridin-4-yl 1625 Et O O 3-chloro-2-(trifluoro- 1-(pyridin-2-yl)ethyl 3.33^([a]) 425 methyl)pyridin-4-yl 1626 Et O O 3-chloro-2-(trifluoro- 1-(1,3-thiazol-2-yl)ethyl 3.46^([a]) 431 methyl)pyridin-4-yl 1627 Et O O 3-chloro-2-(trifluoro- (2S)-3-methylbutan-2-yl 4.18^([a]) 390 methyl)pyridin-4-yl 1628 methyl- NMe O 2-chloropyridin-3-yl (2S)-3-methylbutan-2-yl 1.3^([a]) 336 amino 1629 Et O O 2-chloropyridin-3-yl 1-(4,5-dihydro-1,3-thiazol-2- 2.5^([a]) 365 yl)ethyl 1630 Et O O 2,5-dichlorothiophen-3-yl cyclohexyl 4.92^([a]) 373 1631 Et O O 2,5-dichlorothiophen-3-yl (2S)-1-(cyclohexylamino)-1- 3.83^([a]) 444 oxopropan-2-yl 1632 Et O O 2,5-dichlorothiophen-3-yl (2S)-1-(methylamino)-1- 2.46^([a]) 376 oxopropan-2-yl 1633 Et O O 2-chloropyridin-3-yl (3Z)-3-(methoxyimino)butan-2-yl 2.8^([a]) 351 1634 Et O O 2-chloropyridin-3-yl 1,1′-bi(cyclopropyl)-2-yl 3.13^([a]) 332 1635 Et O O 2-chloropyridin-3-yl 2-(propan-2-yl)cyclopropyl 3.53^([a]) 334 1636 Et O O 2-chloropyridin-3-yl (3Z)-3-(ethoxyimino)butan-2-yl 3.29^([a]) 365 1637 Et O O 2-chloropyridin-3-yl 1-(1-methyl-1H-imidazol-2- 0.93^([a]) 360 yl)ethyl 1638 Et O O 2-chloropyridin-3-yl 1-[5-chloro-4-(trifluoromethyl)- 3.9^([a]) 459 pyridin-2-yl]ethyl 1639 Et O O 2-chloropyridin-3-yl 1-(4,6-dichloropyridin-2- 3.7^([a]) 425 yl)ethyl 1640 Et O O 1-(difluoromethyl)-1H- 1-cyclobutylethyl 3.56^([a]) 339 pyrazol-5-yl 1641 Et O O 2-chloropyridin-3-yl 1-ethylcyclopropyl 3.13^([a]) 320 1642 Et O O 2-chloropyridin-3-yl 1-(cyclopropylmethyl)- 3.53^([a]) 346 cyclopropyl 1643 Et O O 2-chloropyridin-3-yl (2S)-1-phenylpropan-2-yl 3.5^([a]) 370 1644 Et O O 1-(difluoromethyl)-1H- (1S)-1-(1,3-thiazol-2-yl)ethyl 2.51^([a]) 368 pyrazol-5-yl 1645 Et O O 1-(difluoromethyl)-1H- (2R)-3-methylbutan-2-yl 3.27^([a]) 327 pyrazol-5-yl 1646 Et O O 1-(difluoromethyl)-1H- (1S)-1-(pyridin-2-yl)ethyl 2.55^([a]) 362 pyrazol-5-yl 1647 Et O O 1-(difluoromethyl)-1H- (1R)-1-cyclopropylethyl 3.01^([a]) 325 pyrazol-5-yl 1648 Et O O 5-chloro-3-ethyl-1-methyl- 1-cyclobutylethyl 3.94^([a]) 365 1H-pyrazol-4-yl 1649 Et O O 2-chloropyridin-3-yl (1S)-1-(2,6-dichlorophenyl)ethyl 3.8^([a]) 425 1650 Et O O 4-chloro-1,3-thiazol-5-yl (2S)-3-methylbutan-2-yl 328

Chiral groups in table 1 show those R and/or S values, which can be found in the examples IUPAC names (product orientated chirality specification).

Abbreviations for isomers and tautomers: I1 means isomer 1; I2 means isomer 2; T1 means tautomer 1; T2 means tautomer 2.

Me=methyl, Et=ethyl, nPr=n-propyl, iPr=propan-2-yl, cPr=cyclopropyl, nBu=n-butyl, iBu=2-methylpropyl, sBu=sec-butyl, tBu=tert-butyl, cBu=cyclobutyl, Pn=pentyl, Hx=hexyl, cHx=cyclohexyl, OMe=methoxy, allyl=prop-2-en-1-yl, propargyl=prop-2-yn-1-yl, MeOEt=methoxyethyl, EtOEt=ethoxyethyl, F₃iPr=1,1,1-trifluoropropan-2-yl

Measurement of logP values was performed according EEC directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on reversed phase columns with the following methods:

^([a]) measurement of LC-MS was done at pH 2.7 with 0.1% formic acid in water and with acetonitrile (contains 0.1% formic acid) as eluent with a linear gradient from 10% acetonitrile to 95% acetonitrile. ^([b]) Measurement was done at pH 7.5 with 0.005 molar aqueous KH₂PO₄ buffer and acetonitrile as eluent. ^([c]) Measurement was done at pH 2.3 with 0.1% (w/w) phosphoric acid and acetonitrile as eluent. Calibration was done with not branched alkan2-ones (with 3 to 16 carbon atoms) with known logP-values (measurement of logP values using retention times with linear interpolation between successive alkanones). Lambda_(max) values were determined using UV-spectra from 200 nm to 400 nm and the peak values of the chromatographic signals. In table 1, M⁺H (or M H) means the molecular ion peak, plus or minus 1 a.m.u. (atomic mass unit) respectively, as observed in mass spectroscopy and M (APCI⁺) means the molecular ion peak as it was found via positive atmospheric pressure chemical ionization in mass spectroscopy. *M-1 was measured for these examples.

Use Examples Example A Plasmopara Test (Grapevines)/Preventive

-   Solvent: 24.5 parts by weight of acetone     -   24.5 parts by weight of dimethylacetamide -   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Plasmopara viticola and then remain for 1 day in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of 100%. The plant is subsequently placed for 4 days in a greenhouse at approximately 21° C. and a relative atmospheric humidity of approximately 90%. The plants are then misted and placed for 1 day in an incubation cabinet. The test is evaluated 6 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

Under these conditions, good (at least 70%) or total protection is observed at a dose of 100 ppm with the following compounds according to the invention: 6, 34, 66, 72, 116, 124, 232, 245, 263, 292, 329, 334, 380, 543, 560, 821, 907, 909, 913, 924, 933, 934, 942, 952, 958, 959, 960, 978, 981, 984, 984, 989, 1123, 1146, 1162, 1167, 1171, 1189, 1198, 1253, 1278, 1381, 1445, 1449, 1451, 1456, 1471, 1491, 1491, 1545, 1551, 1607, 1612, 1634, 1639, 1641, 1642, 1644, 1645, 1646, 1673, 1676, 1677, 1688.

Example B In Vivo Test on Alternaria brassicae (Leaf Spot of Crucifers)

The active ingredients tested are prepared by homogenization in a mixture of acetone/Tween/DMSO, then diluted with water to obtain the desired active material. Radish plants (Perrot variety), sown on a 50/50 peat soil-pozzolana substrate in starter cups and grown at 18-20° C., are treated at the cotyledon stage by spraying with the active ingredient prepared as described above. Plants, used as controls, are treated with the mixture of acetone/Tween/water not containing the active material. After 24 hours, the plants are contaminated by spraying them with an aqueous suspension of Alternaria brassicae spores (40,000 spores per cm³). The spores are collected from a 12 to 13 days-old culture. The contaminated radish plants are incubated for 6-7 days at about 18° C., under a humid atmosphere. Grading is carried out 6 to 7 days after the contamination, in comparison with the control plants.

Under these conditions, good protection (at least 70%) is observed at a dose of 500 ppm with the following compounds according to the invention: 155, 170, 954 and 1024.

Example C In Vivo Test on Sphaerotheca fuliginea (Cucurbits Powdery Mildew)

The active ingredients tested are prepared by homogenization in a mixture of acetone/Tween/DMSO, then diluted with water to obtain the desired active material. Gherkin plants (Vert petit de Paris variety) in starter cups, sown on a 50/50 peat soil-pozzolana substrate and grown at 20° C./23° C., are treated at the cotyledon Z10 stage by spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material. After 24 hours, the plants are contaminated by spraying them with an aqueous suspension of Sphaerotheca fuliginea spores (100 000 spores per ml). The spores are collected from a contaminated plants. The contaminated gherkin plants are incubated at about 20° C./25° C. and at 60/70% relative humidity. Grading (% of efficacy) is carried out 12 days after the contamination, in comparison with the control plants.

Under these conditions, good (at least 70%) or total protection is observed at a dose of 500 ppm with the following compounds according to the invention: 94, 98, 105, 148, 149, 158, 187, 817, 818, 833, 834, 835, 836, 855, 857, 858, 868, 954, 1013, 1016, 1026 and 1085.

Example D In Vivo Test on Pyrenophora teres (Barley Net Blotch)

The active ingredients tested are prepared by homogenization in a mixture of acetone/Tween/DMSO, then diluted with water to obtain the desired active material concentration. Barley plants (Express variety), sown on a 50/50 peat soil-pozzolana substrate in starter cups and grown at 12° C., are treated at the 1-leaf stage (10 cm tall) by spraying with the active ingredient prepared as described above. Plants, used as controls, are treated with an aqueous solution not containing the active material. After 24 hours, the plants are contaminated by spraying them with an aqueous suspension of Pyrenophora teres spores (12,000 spores per ml). The spores are collected from a 12-day-old culture. The contaminated barley plants are incubated for 24 hours at about 20° C. and at 100% relative humidity, and then for 12 days at 80% relative humidity. Grading is carried out 12 days after the contamination, in comparison with the control plants.

Under these conditions, good (at least 70%) is observed at a dose of 500 ppm with the following compounds according to the invention: 605, 606, 824 and 948.

Example E In Vivo Test on Mycosphaerella graminicola (Wheat Leaf Spot)

The active ingredients tested are prepared by homogenization in a mixture of acetone/tween/DMSO, then diluted with water to obtain the desired active material concentration. Wheat plants (Scipion variety), sown on a 50/50 peat soil-pozzolana substrate in starter cups and grown at 12° C., are treated at the 1-leaf stage (10 cm tall) by spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material. After 24 hours, the plants are contaminated by spraying them with an aqueous suspension of Mycosphaerella graminicola spores (500 000 spores per ml). The spores are collected from a 7-day-old culture. The contaminated wheat plants are incubated for 72 hours at 18° C. and at 100% relative humidity, and then for 21 to 28 days at 90% relative humidity. Grading (% of efficacy) is carried out 21 to 28 days after the contamination, in comparison with the control plants.

Under these conditions, good (at least 70%) or total protection is observed at a dose of 500 ppm with the following compounds according to the invention: 156, 158, 364, 435, 644, 645, 951, 1023 and 1032.

Example F In Vivo Test on Pyricularia grisea (Rice Blast)

The active ingredients tested are prepared by homogenization in a mixture of acetone/Tween/DMSO, then diluted with water to obtain the desired active material concentration. Rice plants (Koshihikari variety), sown on a 50/50 peat soil-pozzolana substrate in starter cups and grown at 25° C., are treated at the 2-leaf stage (13-15 cm tall) by spraying with the active ingredient prepared as described above. Plants, used as controls, are treated with the mixture of acetone/Tween/DMSO/water not containing the active material. After 24 hours, the plants are contaminated by spraying them with an aqueous suspension of Pyricularia grisea spores (30,000 spores per ml). The spores are collected from a 17-day-old culture and are suspended in water containing 2.5 g/l of gelatine. The contaminated Rice plants are incubated for 72 hours at about 25° C. and at 100% relative humidity, and then for 3 days at 25° C. at 80% relative humidity during the day and 20% relative humidity during the night. Grading (% of efficacy) is carried out 6 days after the contamination, in comparison with the control plants.

Under these conditions, good (at least 70%) or total protection is observed at a dose of 500 ppm with the following compounds according to the invention: 174, 364, 659, 827 and 955.

Example G Phytophthora Test (Tomato)/Preventive

-   Solvent: 49 parts by weight of N,N-Dimethylformamide -   Emulsifier: 1 part by weight of Alkylarylpolyglycolether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of Phytophthora infestans. The plants remain for one day in an incubation cabinet at approximately 22° C. and a relative atmospheric humidity of 100%. Then the plants are placed in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of 96%. The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

In this test the following compounds according to the invention showed efficacy of 70% or even higher at a concentration of 500 ppm of active ingredient: 5, 6, 15, 21, 22, 23, 24, 27, 32, 33, 34, 35, 36, 48, 52, 57, 58, 59, 60, 61, 63, 64, 65, 66, 72, 74, 79, 82, 85, 123, 124, 210, 212, 213, 214, 216, 217, 219, 221, 223, 232, 233, 234, 236, 239, 241, 242, 247, 252, 256, 259, 260, 263, 264, 266, 267, 268, 269, 270, 271, 275, 276, 279, 281, 284, 285, 287, 289, 291, 292, 294, 295, 297, 298, 299, 300, 301, 303, 304, 305, 306, 307, 309, 312, 313, 316, 317, 318, 321, 322, 324, 328, 329, 330, 332, 334, 341, 343, 348, 349, 356, 357, 360, 380, 388, 426, 471, 472, 473, 474, 476, 477, 487, 495, 496, 530, 531, 541, 543, 550, 551, 552, 553, 554, 559, 560, 561, 562, 571, 586, 593, 595, 619, 620, 687, 691, 696, 705, 706, 708, 714, 717, 720, 721, 722, 723, 724, 725, 728, 731, 734, 736, 737, 739, 741, 742, 746, 750, 751, 755, 760, 762, 763, 764, 768, 772, 774, 778, 793, 798, 799, 800, 803, 804, 805, 806, 811, 819, 821, 823, 826, 840, 842, 859, 870, 878, 880, 881, 892, 894, 898, 899, 903, 904, 905, 907, 908, 909, 913, 914, 914, 915, 916, 923, 924, 931, 931, 932, 933, 934, 938, 939, 940, 957, 958, 959, 960, 961, 970, 974, 976, 978, 980, 981, 986, 988, 989, 996, 997, 998, 1000, 1003, 1004, 1006, 1007, 1008, 1038, 1049, 1050, 1051, 1052, 1054, 1055, 1059, 1062, 1064, 1065, 1067, 1073, 1079, 1080, 1081, 1082, 1083, 1101, 1114, 1115, 1116, 1117, 1118, 1119, 1120, 1121, 1123, 1124, 1125, 1127, 1128, 1130, 1131, 1133, 1135, 1136, 1141, 1142, 1144, 1146, 1147, 1148, 1149, 1150, 1151, 1152, 1156, 1158, 1159, 1161, 1162, 1163, 1166, 1167, 1169, 1172, 1173, 1174, 1175, 1178, 1179, 1181, 1182, 1183, 1184, 1185, 1186, 1188, 1189, 1190, 1191, 1192, 1193, 1194, 1195, 1197, 1198, 1201, 1202, 1203, 1204, 1205, 1206, 1208, 1212, 1213, 1216, 1218, 1222, 1223, 1224, 1225, 1227, 1228, 1230, 1231, 1232, 1239, 1240, 1241, 1242, 1243, 1244, 1246, 1247, 1248, 1251, 1252, 1253, 1254, 1255, 1260, 1261, 1262, 1263, 1266, 1269, 1270, 1271, 1273, 1275, 1276, 1278, 1279, 1280, 1281, 1284, 1291, 1292, 1293, 1294, 1297, 1307, 1314, 1322, 1324, 1331, 1355, 1356, 1365, 1380, 1381, 1394, 1404, 1406, 1413, 1418, 1419, 1425, 1438, 1440, 1442, 1443, 1445, 1446, 1448, 1449, 1454, 1458, 1460, 1462, 1464, 1466, 1467, 1467, 1468, 1471, 1471, 1489, 1491, 1504, 1513, 1520, 1532, 1536, 1539, 1545, 1546, 1547, 1549, 1551, 1563, 1564, 1566, 1584, 1590, 1593, 1599, 1600, 1606, 1607, 1608, 1611, 1612, 1616, 1618, 1620, 1629, 1632, 1633, 1633, 1634, 1634, 1635, 1635, 1636, 1637, 1638, 1639, 1640, 1641, 1642, 1644, 1645, 1646, 1647, 1652, 1657, 1664, 1673, 1676, 1677, 1679, 1681, 1682, 1683, 1684, 1685, 1686, 1687, 1688, 1689.

Example H Alternaria Test (Tomato)/Preventive

-   Solvent: 49 parts by weight of N,N-Dimethylformamide -   Emulsifier: 1 part by weight of Alkylarylpolyglycolether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of Alternaria solani. The plants remain for one day in an incubation cabinet at approximately 22° C. and a relative atmospheric humidity of 100%. Then the plants are placed in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of 96%. The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control while an efficacy of 100% means that no disease is observed.

In this test the following compounds according to the invention showed efficacy of 70% or even higher at a concentration of 500 ppm of active ingredient: 28, 121, 296, 385, 992.

Example I Leptosphaeria Test (Wheat)/Preventive

-   Solvent: 49 parts by weight of N,N-Dimethylformamide -   Emulsifier: 1 part by weight of Alkylarylpolyglycolether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with a preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of Leptosphaeria nodorum. The plants remain for 48 hours in an incubation cabinet at 22° C. and a relative atmospheric humidity of 100%. Then the plants are placed in a greenhouse at a temperature of approximately 22° C. and a relative atmospheric humidity of approximately 90%. The test is evaluated 7-9 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

In this test the following compounds according to the invention showed efficacy of 70% or even higher at a concentration of 500 ppm of active ingredient: 284, 286, 296, 1054, 1067.

Example J Puccinia Test (Wheat)/Preventive

-   Solvent: 49 parts by weight of N,N-Dimethylformamide -   Emulsifier: 1 part by weight of Alkylarylpolyglycolether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of Puccinia recondita. The plants remain for 48 hours in an incubation cabinet at 22° C. and a relative atmospheric humidity of 100%. Then the plants are placed in a greenhouse at a temperature of approximately 20° C. and a relative atmospheric humidity of approximately 80%. The test is evaluated 7-9 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control while an efficacy of 100% means that no disease is observed.

In this test the following compounds according to the invention showed efficacy of 70% or even higher at a concentration of 500 ppm of active ingredient: 69, 70, 73, 272, 273, 296, 302, 545, 546, 589, 591, 597, 843, 992, 993.

Example K In Vivo Test on Peronospora parasitica (Crucifer Downy Mildew)

The active ingredients tested are prepared by homogenization in a mixture of acetone/Tween/DMSO, then diluted with water to obtain the desired active material concentration. Cabbage plants (Eminence variety) in starter cups, sown on a 50/50 peat soil-pozzolana substrate and grown at 18-20° C., are treated at the cotyledon stage by spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material. After 24 hours, the plants are contaminated by spraying them with an aqueous suspension of Peronospora parasitica spores (50 000 spores per ml). The spores are collected from infected plant. The contaminated cabbage plants are incubated for 5 days at 20° C., under a humid atmosphere. Grading is carried out 5 days after the contamination, in comparison with the control plants.

Under these conditions, good (at least 70%) or total protection is observed at a dose of 500 ppm with the following compounds: 17, 21, 24, 85, 88, 89, 93, 96, 100, 101, 103, 104, 105, 112, 116, 117, 128, 130, 133, 135, 138, 139, 140, 141, 142, 143, 144, 145, 146, 148, 149, 152, 153, 154, 155, 156, 157, 158, 160, 161, 163, 167, 169, 172, 174, 180, 181, 182, 183, 186, 187, 188, 189, 190, 191, 193, 194, 195, 196, 199, 203, 204, 245, 334, 341, 343, 410, 427, 430, 433, 440, 442, 443, 444, 448, 450, 452, 453, 454, 455, 456, 610, 611, 612, 614, 615, 628, 633, 635, 636, 637, 639, 641, 642, 644, 645, 646, 647, 648, 650, 653, 655, 656, 657, 658, 659, 660, 661, 663, 669, 671, 673, 674, 675, 676, 678, 679, 680, 683, 684, 685, 686, 743, 767, 769, 770, 771, 772, 773, 780, 784, 792, 817, 824, 833, 834, 835, 853, 854, 855, 863, 864, 868, 872, 881, 882, 884, 886, 918, 921, 922, 925, 931, 941, 942, 945, 949, 950, 951, 952, 953, 954, 955, 1016, 1020, 1024, 1026, 1029, 1030, 1031, 1107 and 1109.

Example L Boophilus microplus—Test Injection)

-   Solvent: dimethyl sulfoxide

To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with solvent to the desired concentration. Five adult engorged female ticks (Boophilus microplus) are injected with 1 μl compound solution into the abdomen. Ticks are transferred into replica plates and incubated in a climate chamber for a period of time. Egg deposition of fertile eggs is monitored. After 7 days, mortality in % is determined. 100% means that all eggs are infertile; 0% means that all eggs are fertile.

In this test for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 20 μg/animal: 239

Example M Phaedon cochleariae—Test; (PHAECO Spray Application)

-   Solvent: 78.0 parts by weight of acetone     -   1.5 parts by weight of dimethylformamide -   Emulsifier: 0.5 parts by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. Chinese cabbage (Brassica pekinesis) leaf-disks are sprayed with a preparation of the active ingredient of the desired concentration. Once dry, the leaf disks are infested with mustard beetle larvae (Phaedon cochleariae). After 7 days mortality in % is determined. 100% means that all beetle larvae have been killed and 0% means that none of the beetle larvae have been killed.

In this test for example, the following compounds from the preparation examples showed good activity of 83% at an application rate of 500 g/ha: 40, 1028

In this test for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 500 g/ha: 957, 979, 1475, 1591.

Example N Myzus persicae—Test; (MYZUPE Spray Application)

-   Solvent: 78.0 parts by weight acetone     -   1.5 parts by weight dimethylformamide -   Emulsifier: 0.5 parts by weight alkylarylpolyglycolether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. Chinese cabbage (Brassica pekinesis) leaf-disks infected with all instars of the green peach aphid (Myzus persicae), are sprayed with a preparation of the active ingredient at the desired concentration. After 6 days mortality in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed.

In this test for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 500 g/ha: 597

In this test for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 500 g/ha: 62, 600, 1244 

The invention claimed is:
 1. An aminopropenoate of formula (I)

in which R represents one of the following groups R^(A), R^(B) or R^(C)

n represents 0, 1, 2, 3 or 4, m represents 1, 2, 3 or 4, t represents 0 or 1, Y¹ represents S, O or NR⁵, Y² represents O, S or NR⁶, Y³ represents S, O or NR⁸, Y⁴ represents a bond or O, S or NR⁹, Y⁵ represents SO or SO₂, in case that Y² represents NR⁶, then R⁶ and R¹ together with the nitrogen atom to which they are linked may form a 5- to 7-membered, saturated or unsaturated, carbo- or heterocycle comprising up to 3 heteroatoms, which cycle may also include one of the groups C(═O) and C(═S), in case that Y⁴ represents NR⁹, then R⁹ and R⁷ together with the nitrogen atom to which they are linked may form a 5- to 7-membered, saturated or unsaturated, carbo- or heterocycle comprising up to 3 heteroatoms, which cycle may also include one of the groups C(═O) and C(═S), R¹ represents hydrogen, C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₃-C₈-cycloalkyl-C₁-C₈-alkyl, C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl, C₁-C₈-halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl, C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl, benzotriazolyl, aryl-C₃-C₈-cycloalkyl which can be substituted by up to 5 groups Q; and, provided that when Y² does not represent NH, R¹ can also represent aryl which can be substituted by up to 5 groups Q, or aryl-C₁-C₈-alkyl which can be substituted by up to 5 groups Q; Het represents one of the heterocycles Het 48 to Het 50:

R² and R³, which can be the same or different, independently of one another represent hydrogen, halogen, CN, NH₂, NO₂, C₁-C₈-alkyl, C₁-C₈-hydroxyalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl, C₂-C₈-alkenyl, C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different, C₂-C₈-alkynyl, C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl, C₃-C₈-halogeno-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkoxy-C₂-C₈-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkynyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl, C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl, C₁-C₈alkylsulfinyl-C₁-C₈-alkyl, C₁-C₈-alkylsulfonyl-C₁-C₈-alkyl, amino-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl, di-(C₁-C₈-alkyl)amino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl, phenyl which can be substituted by up to 5 groups Q, or phenyl-C₂-C₄-alkynyl, which can be substituted in the phenyl moiety by up to 5 groups Q, R² and R³ also together with the carbon atom to which they are linked can form a C₃-C₇-cycloalkyl, which may be substituted by 1 to 4 identical or different substituents selected from halogen, OH, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl, C₁-C₄-alkoxy, alkylthio or phenyl, or can form a C₅-C₁₀-bicycloalkyl, a 2,3-dihydro-1H-indene-1-yl or a decahydronaphthalenyl, R⁴ represents aryl or a heterocycle E 1 to E 144:

R⁴ also represents hydrogen or halogen when n represents 1, 2, 3 or 4, R⁵ represents hydrogen, OH, C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl, C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl, halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl, C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl, aryl which can be substituted by up to 5 groups Q, aryl-C₁-C₈-alkyl which can be substituted by up to 5 groups Q, or aryl-C₃-C₈-cycloalkyl which can be substituted by up to 5 groups Q; R⁶ represents hydrogen, OH, C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl, C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl, halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl, C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl, C₁-C₈-alkoxy, C₃-C₈-cycloalkoxy, C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkoxy, C₂-C₈-alkenyl-C₁-C₈-alkoxy, C₂-C₈-alkynyl-C₁-C₈-alkoxy, C₁-C₈-halogeno-C₃-C₈-cycloalkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkenyloxy, C₁-C₈-alkoxy-C₁-C₈-alkoxy, C₃-C₈-cycloalkoxy-C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy-C₁-C₈-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkoxy, C₁-C₈-alkylamino-C₁-C₈-alkoxy, C₁-C₈-halogenoalkylamino-C₁-C₈-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkylamino-C₁-C₈-alkoxy, C₁-C₈-trialkylsilyl-C₁-C₈-alkoxy, aryloxy which can be substituted by up to 5 groups Q, benzyloxy which can be substituted by up to 5 groups Q, C₁-C₈-alkylamino, (C₁-C₈-alkyl)carbonylamino, C₃-C₈-cycloalkylamino, C₁-C₈-halogenoalkylamino comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkylamino, C₂-C₈-alkenyl-C₁-C₈-alkylamino, C₂-C₈-alkynyl-C₁-C₈-alkylamino, halogeno-C₃-C₈-cycloalkylamino comprising up to 9 halogen atoms which can be the same or different, arylamino which can be substituted by up to 5 groups Q, benzylamino which can be substituted by up to 5 groups Q, or aryl-C₃-C₈-cycloalkyl which can be substituted by up to 5 groups Q; R⁷ represents hydrogen, C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl, halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl, C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl, phenyl or naphthyl, each of which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q, or phenyl-C₁-C₂-alkylimino, R⁷ also represents CN, if R is R^(B), t is 0 and Y⁴ is a bond, R⁸ represents hydrogen, OH, C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl, C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl, C₁-C₈-halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-cycloalkoxy-C₁-C₈-alkyl, C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl, phenyl which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q; C₁-C₈-alkoxy, C₃-C₈-cycloalkoxy, C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkoxy, C₂-C₈-alkenyl-C₁-C₈-alkoxy, C₂-C₈-alkynyl-C₁-C₈-alkoxy, C₁-C₈-halogeno-C₃-C₈-cycloalkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkenyloxy, C₁-C₈-alkoxy-C₁-C₈-alkoxy, C₃-C₈-cycloalkoxy-C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy-C₁-C₈-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkoxy, C₁-C₈-alkylamino-C₁-C₈-alkoxy, C₁-C₈-halogenoalkylamino-C₁-C₈-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkylamino-C₁-C₈-alkoxy, C₁-C₈-trialkylsilyl-C₁-C₈-alkoxy, aryloxy which can be substituted by up to 5 groups Q, or benzyloxy which can be substituted by up to 5 groups Q, R⁹ represents hydrogen, OH, C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl, C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl, C₃-C₈-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl, C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl, phenyl which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q; C₁-C₈-alkoxy, C₃-C₈-cycloalkoxy, C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkoxy, C₂-C₈-alkenyl-C₁-C₈-alkoxy, C₂-C₈-alkynyl-C₁-C₈-alkoxy, halogeno-C₃-C₈-cycloalkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkenyloxy, C₁-C₈-alkoxy-C₁-C₈-alkoxy, C₃-C₈-cycloalkoxy-C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy-C₁-C₈-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkoxy, C₁-C₈-alkylamino-C₁-C₈-alkoxy, C₁-C₈-halogenoalkylamino-C₁-C₈-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkylamino-C₁-C₈-alkoxy, C₁-C₈-trialkylsilyl-C₁-C₈-alkoxy, phenyloxy which can be substituted by up to 5 groups Q, or benzyloxy which can be substituted by up to 5 groups Q, Q which can be the same or different, independently represents halogen, CN, NO₂, C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylsulfanyl, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, tri(C₁-C₈)alkylsilyl or tri(C₁-C₈)alkylsilyl-C₁-C₈-alkyl, or two vicinal substituents Q may be —OCH₂O—, —OCF₂O—, —O(CH₂)₂O—, —O(CF₂)₂O— or —N═CH—S—, Z¹, Z², Z³, Z⁴ Z⁵, Z⁶, Z⁷, Z⁸, Z⁹, Z¹⁰ and Z¹¹, which can be the same or different, independently of one another represent hydrogen, halogen, NO₂, CN, OH, SH, NH₂, SF₅, C₁-C₈-alkyl, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different and optionally in addition one hydroxy group, C₁-C₈-alkylamino, di-C₁-C₈-alkylamino, C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylsulfanyl, C₁-C₈-halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different, C₂-C₈-alkenyl, C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different, C₂-C₈-alkynyl, C₂-C₈-halogenoalkynyl comprising up to 9 halogen atoms which can be the same or different, C₂-C₈-alkenyloxy, C₂-C₈-halogenoalkenyloxy comprising up to 9 halogen atoms which can be the same or different, C₂-C₈-alkynyloxy, C₂-C₈-halogenoalkynyloxy comprising up to 9 halogen atoms which can be the same or different, C₂-C₈-alkenylsulfanyl, C₂-C₈-alkynylsulfanyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₈-alkyl, C₃-C₇-halogenocyclo-alkyl comprising up to 9 halogen atoms which can be the same or different, formyl, formyloxy, formylamino, carbamoyl, N-hydroxycarbamoyl, (hydroxyimino)-C₁-C₈-alkyl, C₁-C₈-alkylcarbonyl, C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different, (C₃-C₇-cycloalkyl)carbonyl, C₁-C₈-alkylcarbamoyl, di-C₁-C₈-alkylcarbamoyl, N—C₁-C₈-alkoxycarbamoyl, C₁-C₈-alkoxycarbamoyl, N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, C₁-C₈-alkoxycarbonyl, C₁-C₈-halogenoalkoxy-carbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylaminocarbonyl, di-(C₁-C₈-alkyl)aminocarbonyl, C₁-C₈-alkylcarbonyloxy, C₁-C₈-halogenoalkylcarbonyloxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylcarbonylamino, C₁-C₈-halogenoalkylcarbonylamino comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylaminocarbonyloxy, di-(C₁-C₈-alkyl)aminocarbonyloxy, C₁-C₈-alkoxycarbonyloxy, C₁-C₈-alkylsulphinyl, C₁-C₈-halogenoalkylsulphinyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulphonyl, C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkoxyimino, (C₁-C₈-alkylimino)-C₁-C₈-alkyl, (C₁-C₈alkoxyimino)-C₁-C₈-alkyl, (C₁-C₈-alkenyloxyimino)-C₁-C₈-alkyl, (C₂-C₈-alkynyloxyimino)-C₁-C₈-alkyl, a (benzyloxyimino)-C₁-C₈-alkyl, tri-(C₁-C₈-alkyl)silyl, tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, benzyloxy which can be substituted by up to 5 groups Q, benzylsulfanyl which can be substituted by up to 5 groups Q, benzylamino which can be substituted by up to 5 groups Q, phenyl which can be substituted by up to 5 groups Q, naphthyl which can be substituted by up to 6 groups Q, phenoxy which can be substituted by up to 5 groups Q, phenylamino which can be substituted by up to 5 groups Q, phenylsulfanyl which can be substituted by up to 5 groups Q, or phenylmethylene which can be substituted by up to 5 groups Q, or two vicinal substituents Z together with the consecutive carbon atoms to which they are linked form a 5- or 6-membered, saturated or unsaturated, carbo- or heterocycle comprising up to 3 heteroatoms, which can be substituted by up to four groups Q which can be the same or different and the other substituents Z as defined above, or two geminal substituents Z together with the carbon atom to which they are linked can also be fused to represent C(═O); C(═S), or C₃-C₉-cycloalkyl; G¹ and G² which can be the same or different, independently of one another represent hydrogen, CN, OH, NH₂, C₁-C₈-alkyl, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylamino, di-C₁-C₈-alkylamino, C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₂-C₈-alkenyl, C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different, C₂-C₈-alkynyl, C₂-C₈-halogenoalkynyl comprising up to 9 halogen atoms which can be the same or different, C₂-C₈-alkenyloxy, C₂-C₈-halogenoalkenyloxy comprising up to 9 halogen atoms which can be the same or different, C₂-C₈-alkynyloxy, C₂-C₈-halogenoalkynyloxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₈-alkyl, C₁-C₇-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, formyl, carbamoyl, (hydroxyimino)-C₁-C₈-alkyl, C₁-C₈-alkylcarbonyl, C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylcarbamoyl, C₁-C₈-alkoxycarbonyl, C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylaminocarbonyl, di-C₁-C₈-alkylaminocarbonyl, C₁-C₈-alkylsulphonyl, C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms which can be the same or different, (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl, (C₁-C₈-alkenyloxyimino)-C₁-C₈-alkyl, (C₂-C₈-alkynyloxyimino)-C₁-C₈-alkyl, (benzyloxyimino)-C₁-C₈-alkyl, tri(C₁-C₈-alkyl)silyl, tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, benzyloxy which can be substituted by up to 5 groups Q, benzylamino which can be substituted by up to 5 groups Q, phenyl which can be substituted by up to 5 groups Q; naphthyl which can be substituted by up to 6 groups Q, phenoxy which can be substituted by up to 5 groups Q, phenylamino which can be substituted by up to 5 groups Q, or phenylmethylene which can be substituted by up to 5 groups Q, provided that when n represents 1 then R², R³ and R⁴ do not represent simultaneously a hydrogen atom, or a salt, N-oxide, metallic complex, metalloidic complex or an optically active or geometric isomer thereof.
 2. A composition, comprising at least one aminopropenoate of the formula (I) according to claim 1, and one or more extenders, surfactants, or combinations thereof.
 3. A method for controlling fungi or bacteria, comprising applying at least one aminopropenoate of the formula (I) according to claim 1 to the fungi or bacteria, their habitat, or combinations thereof.
 4. A process for preparing a composition comprising mixing at least one aminopropenoate of the formula (I) according to claim 1 with one or more extenders, surfactants, or combinations thereof.
 5. A method for controlling fungi or bacteria on a transgenic plant, comprising applying at least one aminopropenoate of the formula (I) according to claim 1 to the transgenic plant, its seed, its habitat, or combinations thereof.
 6. The aminopropenoate of the formula (I) according to claim 1, wherein R represents R^(A).
 7. The aminopropenoate of the formula (I) according to claim 1, wherein R represents R^(B).
 8. The aminopropenoate of the formula (I) according to claim 6, wherein n represents 0, 1 or
 2. 9. The aminopropenoate of the formula (I) according to claim 1, wherein m represents 1 or
 2. 10. The aminopropenoate of the formula (I) according to claim 1, wherein Y¹ is S or O.
 11. The aminopropenoate of the formula (I) according to claim 1, wherein Y² represents O or NR⁶, wherein R⁶ represents hydrogen, C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl, C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl, C₁-C₈-halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl, C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl, or C₁-C₈-alkoxy.
 12. The aminopropenoate of the formula (I) according to claim 1, wherein Y³ represents O or NR⁸, wherein R⁸ represents hydrogen, C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl, C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl, C₁-C₈-halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl, C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy, C₁-C₆-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₆-alkoxy, C₂-C₆-alkenyl-C₁-C₆-alkoxy, C₂-C₆-alkynyl-C₁-C₆-alkoxy, C₁-C₆-halogeno-C₃-C₆-cycloalkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkenyloxy, C₁-C₆-alkoxy-C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy-C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy-C₁-C₆-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulfanyl-C₁-C₆-alkoxy, C₁-C₆-alkylamino-C₁-C₆-alkoxy, C₁-C₆-halogenoalkylamino-C₁-C₆-alkoxy comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkylamino-C₁-C₆-alkoxy, C₁-C₆-trialkylsilyl-C₁-C₆-alkoxy, aryloxy which can be substituted by up to 5 groups Q, or benzyloxy which can be substituted by up to 5 groups Q.
 13. The aminopropenoate of the formula (I) according to claim 1, wherein Y⁴ represents a bond, O or NR⁹, wherein R⁹ represents hydrogen or C₁-C₆-alkyl.
 14. The aminopropenoate of the formula (I) according to claim 1, wherein R¹ represents hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₂-C₄-alkenyl, C₂-C₄-alkynyl, or C₁-C₄-alkoxy-C₁-C₄-alkyl.
 15. The aminopropenoate of the formula (I) according to claim 1, wherein R⁴ is selected from E 1 to E 48, E 52 to E 56, E 63, E 64, E 69 to E 77, E 98 to E 100, E 105, E 106, E 109 to E 112, E 129 or E 130, and wherein Z¹, Z², Z³, Z⁴, Z⁵, Z⁶, Z⁷, Z⁸, Z⁹, Z¹⁰ and Z¹¹, which can be the same or different, independently of one another represent hydrogen, halogen, NO₂, CN, OH, SH, NH₂, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, s-butyl, t-butyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, methylamino, ethylamino, dimethylamino, diethylamino, methoxy, ethoxy, trifluoromethoxy, vinyl, allyl, ethinyl, propargyl, cyclopropyl, cyclohexyl, acetyl, C₁-C₃-halogenoalkylcarbonyl comprising up to 5 halogen atoms which can be the same or different, carboxyl, methoxycarbonyl, ethoxycarbonyl, C₁-C₄-alkyl-carbonyloxy, C₁-C₄-alkylcarbonylamino, methylthio, ethylthio, trimethylsilyl, phenyl which can be substituted by up to 3 groups Q, or naphthyl which can be substituted by up to 6 groups Q, or two geminal substituents Z together with the carbon atom to which they are linked can be fused to represent C(═O).
 16. The aminopropenoate of the formula (I) according to claim 1, wherein R⁵ represents hydrogen, OH, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₂-halogenoalkyl comprising up to 5 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₂-alkyl, C₂-C₄-alkenyl-C₁-C₄-alkyl, C₂-C₄-alkynyl-C₁-C₄-alkyl, halogeno-C₃-C₆-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, cyclohexenyl, alkyl, C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, C₁-C₄-halogenoalkoxy-C₁-C₄-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-alkylsulfanyl-C₁-C₄-alkyl, C₁-C₄-alkylamino-C₁-C₄-alkyl, C₁-C₄-halogenoalkylamino-C₁-C₄-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₄-trialkylsilyl-C₁-C₄-alkyl, phenyl or naphthyl, each of which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q.
 17. The aminopropenoate of the formula (I) according to claim 1, wherein R² and R³, which can be the same or different, independently of one another represent hydrogen, halogen, CN, NH₂, C₁-C₆-alkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-cycloalkyl, C₃-C₆-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₂-C₆-alkenyl-C₁-C₆-alkyl, C₂-C₆-alkynyl-C₁-C₆-alkyl, C₃-C₆-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₆-cycloalkoxy-C₁-C₆-alkyl, C₁-C₆-halogenoalkoxy-C₁-C₆-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulfanyl-C₁-C₆-alkyl, C₁-C₆-alkylamino-C₁-C₆-alkyl, C₁-C₆-halogenoalkylamino-C₁-C₆-alkyl comprising up to 9 halogen atoms which can be the same or different, or R₂ and R₃ together with the carbon atom to which they are linked can form a C₃-C₇ cycloalkyl.
 18. An aminopropenoate of the formula (I) according to 1, wherein R⁷ represents hydrogen, CN, C₃-C₆-cycloalkyl, C₁-C₆-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, halogeno-C₃-C₆-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₆-cycloalkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-halogenoalkoxy-C₁-C₆-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-alkylsulfanyl-C₁-C₆-alkyl, C₁-C₆-alkyl, phenyl or naphthyl, each of which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q, or phenyl-C₁-C₂-alkylimino.
 19. The aminopropenoate of the formula (I) according to claim 1, wherein R represents R^(B), wherein t represents 0, Y³ represents O, Y⁴ represents NR⁹, and R⁹ represents hydrogen, C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkyl-C₁-C₈-alkyl, C₂-C₈-alkenyl-C₁-C₈-alkyl, C₂-C₈-alkynyl-C₁-C₈-alkyl, C₁-C₈-halogeno-C₃-C₈-cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₃-C₈-cycloalkoxy-C₁-C₈-alkyl, C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₈-alkylsulfanyl-C₁-C₈-alkyl, C₁-C₈-alkylamino-C₁-C₈-alkyl, C₁-C₈-halogenoalkylamino-C₁-C₈-alkyl comprising up to 9 halogen atoms which can be the same or different, C₃-C₈-cycloalkylamino-C₁-C₈-alkyl, C₁-C₈-trialkylsilyl-C₁-C₈-alkyl, phenyl which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q.
 20. The aminopropenoate of the formula (I) according to claim 1, wherein Q which can be the same or different, independently represents halogen, CN, NO₂, C₁-C₆-alkoxy, C₁-C₆-alkylsulfanyl, C₁-C₆-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C₁-C₆-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, tri(C₁-C₆)alkylsilyl or tri(C₁-C₆)alkylsilyl-C₁-C₆-alkyl. 